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100306-33-0

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100306-33-0 Usage

Chemical Properties

Off-white Cryst

Uses

Different sources of media describe the Uses of 100306-33-0 differently. You can refer to the following data:
1. Intermediate in the preparation of (S)-Norfluoxetine
2. (R)-(+)-3-Chloro-1-phenyl-1-propanol may be used as a building block in the synthesis of antidepressants such as (R)- and (S)-tomoxetine, fluoxetine and nisoxetine. It may also be used in the synthesis of biologically active 2-substituted chromans such as tephrowatsin E.

Check Digit Verification of cas no

The CAS Registry Mumber 100306-33-0 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,0,0,3,0 and 6 respectively; the second part has 2 digits, 3 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 100306-33:
(8*1)+(7*0)+(6*0)+(5*3)+(4*0)+(3*6)+(2*3)+(1*3)=50
50 % 10 = 0
So 100306-33-0 is a valid CAS Registry Number.
InChI:InChI=1/C9H11ClO/c10-7-6-9(11)8-4-2-1-3-5-8/h1-5,9,11H,6-7H2/t9-/m1/s1

100306-33-0 Well-known Company Product Price

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  • TCI America

  • (C2423)  (R)-(+)-3-Chloro-1-phenyl-1-propanol  >98.0%(GC)

  • 100306-33-0

  • 1g

  • 590.00CNY

  • Detail
  • Aldrich

  • (338419)  (R)-(+)-3-Chloro-1-phenyl-1-propanol  98%

  • 100306-33-0

  • 338419-1G

  • 778.05CNY

  • Detail
  • Aldrich

  • (338419)  (R)-(+)-3-Chloro-1-phenyl-1-propanol  98%

  • 100306-33-0

  • 338419-5G

  • 2,402.95CNY

  • Detail

100306-33-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name (1R)-3-Chloro-1-Phenyl-Propan-1-ol

1.2 Other means of identification

Product number -
Other names (1R)-3-chloro-1-phenylpropan-1-ol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:100306-33-0 SDS

100306-33-0Synthetic route

3-chloropropiophenone
936-59-4

3-chloropropiophenone

(1R)-3-chloro-1-phenylpropanol
100306-33-0

(1R)-3-chloro-1-phenylpropanol

Conditions
ConditionsYield
With borane; S-oxaborolidine In tetrahydrofuran at 0℃; for 0.833333h;99%
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; C22H32N4O4S2; water; sodium formate at 40℃; for 0.25h; Air atmosphere; optical yield given as %ee; enantioselective reaction;99%
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; (1R,2R)-9H-fluorene-2,7-disulfonic acid bis-[(2-amino-cyclohexyl)amide]; sodium formate In water at 40℃; for 0.25h; optical yield given as %ee; enantioselective reaction;99%
3-chloropropiophenone
936-59-4

3-chloropropiophenone

A

3-chloro-1-phenylpropanol
100306-34-1

3-chloro-1-phenylpropanol

B

(1R)-3-chloro-1-phenylpropanol
100306-33-0

(1R)-3-chloro-1-phenylpropanol

Conditions
ConditionsYield
With dimethylsulfide borane complex; C23H22BNO3 In tetrahydrofuran at 20℃; for 2h; Reagent/catalyst;A n/a
B 75%
With dimethylsulfide borane complex; (+)-3-exo-amino-7,7-dimethoxynorbornan-2-exo-ol In tetrahydrofuran at 25℃; for 2h;A 65%
B n/a
With dimethylsulfide borane complex; chiral diphenyloxazaborolidine In tetrahydrofuran at 25℃; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
Isopropenyl acetate
108-22-5

Isopropenyl acetate

3-chloro-1-phenyl-propan-1-ol
18776-12-0

3-chloro-1-phenyl-propan-1-ol

A

3-chloro-1-phenylpropanol
100306-34-1

3-chloro-1-phenylpropanol

B

(1R)-3-chloro-1-phenylpropanol
100306-33-0

(1R)-3-chloro-1-phenylpropanol

C

(R)-3-chloro-1-phenyl-1-propyl acetate

(R)-3-chloro-1-phenyl-1-propyl acetate

Conditions
ConditionsYield
With Pseudomonas cepacia lipase immobilized on toyonite; potassium tert-butylate; sodium carbonate; [2,3,4,5-Ph4(η5-C4CNH(i-Pr))]Ru(CO)2Cl In toluene at 25℃; for 168h;A n/a
B n/a
C 31%
With Burkholderia species lipoprotein lipase; C51H77NO17; dextrin In toluene at 25℃; for 6h; Enzymatic reaction; enantioselective reaction;A n/a
B n/a
C n/a
vinyl acetate
108-05-4

vinyl acetate

3-chloro-1-phenyl-propan-1-ol
18776-12-0

3-chloro-1-phenyl-propan-1-ol

A

3-chloro-1-phenylpropanol
100306-34-1

3-chloro-1-phenylpropanol

B

(1R)-3-chloro-1-phenylpropanol
100306-33-0

(1R)-3-chloro-1-phenylpropanol

C

(R)-3-chloro-1-phenyl-1-propyl acetate

(R)-3-chloro-1-phenyl-1-propyl acetate

Conditions
ConditionsYield
With lipase from Pseudomonas fluorescens In hexane at 20℃; for 21h; Resolution of racemate; Enzymatic reaction; optical yield given as %ee; enantioselective reaction;A n/a
B n/a
C 25%
(R)-3-chloro-1-phenyl-1-propyl acetate

(R)-3-chloro-1-phenyl-1-propyl acetate

(1R)-3-chloro-1-phenylpropanol
100306-33-0

(1R)-3-chloro-1-phenylpropanol

Conditions
ConditionsYield
With lipase from Candida rugosa at 20℃; for 5h; pH=8; aq. phosphate buffer; Enzymatic reaction; stereoselective reaction;23%
Phenyl-acetic acid 3-chloro-1-phenyl-propyl ester

Phenyl-acetic acid 3-chloro-1-phenyl-propyl ester

(1R)-3-chloro-1-phenylpropanol
100306-33-0

(1R)-3-chloro-1-phenylpropanol

Conditions
ConditionsYield
In acetonitrile at 27 - 28℃; 0.1 M aq. phosphate buffer (pH 8.0), penicillin G aminohydrolase (PGA);18%
1-Phenyl-3-chlor-propyl-monochloracetat
141987-54-4

1-Phenyl-3-chlor-propyl-monochloracetat

(1R)-3-chloro-1-phenylpropanol
100306-33-0

(1R)-3-chloro-1-phenylpropanol

Conditions
ConditionsYield
With buffer pH 7 lipase from Pseudomonas fluorescens (SAM-2);
1-Phenyl-3-chlor-propyl-monochloracetat
141987-54-4

1-Phenyl-3-chlor-propyl-monochloracetat

A

(1R)-3-chloro-1-phenylpropanol
100306-33-0

(1R)-3-chloro-1-phenylpropanol

B

Chloro-acetic acid (S)-3-chloro-1-phenyl-propyl ester
142037-19-2

Chloro-acetic acid (S)-3-chloro-1-phenyl-propyl ester

Conditions
ConditionsYield
pH 7, Pseudomonas sp. lipase (SAM-2);
3-Cloro-1-phenylpropyl butanoate
293322-40-4

3-Cloro-1-phenylpropyl butanoate

A

3-chloro-1-phenylpropanol
100306-34-1

3-chloro-1-phenylpropanol

B

(1R)-3-chloro-1-phenylpropanol
100306-33-0

(1R)-3-chloro-1-phenylpropanol

Conditions
ConditionsYield
With phosphate buffer; novozyme 435 at 30℃; for 288h; pH=7; Hydrolysis; Title compound not separated from byproducts;
3-chloropropiophenone
936-59-4

3-chloropropiophenone

A

1-Phenyl-1-propanol
93-54-9

1-Phenyl-1-propanol

B

3-chloro-1-phenylpropanol
100306-34-1

3-chloro-1-phenylpropanol

C

(1R)-3-chloro-1-phenylpropanol
100306-33-0

(1R)-3-chloro-1-phenylpropanol

D

1-phenyl-propan-1-one
93-55-0

1-phenyl-propan-1-one

Conditions
ConditionsYield
With Merulius tremellosus ono991 In acetone at 28℃; for 72h; Title compound not separated from byproducts;
3-chloro-1-phenyl-propan-1-ol
18776-12-0

3-chloro-1-phenyl-propan-1-ol

A

3-chloropropiophenone
936-59-4

3-chloropropiophenone

B

(1R)-3-chloro-1-phenylpropanol
100306-33-0

(1R)-3-chloro-1-phenylpropanol

Conditions
ConditionsYield
With Sphingomonas paucimobilis NCIMB 8195 In water; N,N-dimethyl-formamide for 120h;A 21 % Chromat.
B 79 % Chromat.
3-chloro-1-phenyl-propan-1-ol
18776-12-0

3-chloro-1-phenyl-propan-1-ol

2-Methylpropionic anhydride
97-72-3

2-Methylpropionic anhydride

A

3-chloro-1-phenylpropanol
100306-34-1

3-chloro-1-phenylpropanol

B

(1R)-3-chloro-1-phenylpropanol
100306-33-0

(1R)-3-chloro-1-phenylpropanol

C

Isobutyric acid (S)-3-chloro-1-phenyl-propyl ester

Isobutyric acid (S)-3-chloro-1-phenyl-propyl ester

D

(1R)-3-chloro-1-phenylpropyl 2-methylpropanoate

(1R)-3-chloro-1-phenylpropyl 2-methylpropanoate

Conditions
ConditionsYield
With (-)-(Sa) 4-di-n-butylaminopyridine based biaryl; triethylamine In toluene at -95℃; for 15h; Title compound not separated from byproducts.;
3-chloro-1-phenyl-propan-1-ol
18776-12-0

3-chloro-1-phenyl-propan-1-ol

(1R)-3-chloro-1-phenylpropanol
100306-33-0

(1R)-3-chloro-1-phenylpropanol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 93 percent / pyridine; DMAP / CH2Cl2 / 0 - 20 °C
2: aq. phosphate buffer; Novozyme 435 / 288 h / 30 °C / pH 7
View Scheme
Multi-step reaction with 2 steps
1: pyridine / CH2Cl2
2: buffer pH 7 / lipase from Pseudomonas fluorescens (SAM-2)
View Scheme
3-chloro-1-phenyl-propan-1-ol
18776-12-0

3-chloro-1-phenyl-propan-1-ol

A

3-chloro-1-phenylpropanol
100306-34-1

3-chloro-1-phenylpropanol

B

(1R)-3-chloro-1-phenylpropanol
100306-33-0

(1R)-3-chloro-1-phenylpropanol

Conditions
ConditionsYield
at 145 - 180℃; Gas phase; Resolution of racemate; Inert atmosphere;
With Candida antarctica lipase B (Novozym 435) at 45℃; under 150 Torr; for 144h; Resolution of racemate; Enzymatic reaction; Overall yield = 58 %;A n/a
B n/a
Stage #1: 3-chloro-1-phenyl-propan-1-ol With Candida antarctica lipase B (Novozym 435) at 45℃; under 150 Torr; for 144h; Resolution of racemate; Enzymatic reaction;
Stage #2: With ethanol; Candida antarctica lipase B (Novozym 435) for 24h; Enzymatic reaction; Overall yield = 33 %;
A n/a
B n/a
(RS)-3-chloro-1-phenyl-1-propyl acetate
22912-90-9

(RS)-3-chloro-1-phenyl-1-propyl acetate

A

3-chloro-1-phenylpropanol
100306-34-1

3-chloro-1-phenylpropanol

B

(1R)-3-chloro-1-phenylpropanol
100306-33-0

(1R)-3-chloro-1-phenylpropanol

C

(S)-3-chloro-1-phenyl-1-propyl acetate

(S)-3-chloro-1-phenyl-1-propyl acetate

D

(R)-3-chloro-1-phenyl-1-propyl acetate

(R)-3-chloro-1-phenyl-1-propyl acetate

Conditions
ConditionsYield
With Bacillus subtilis esterase In ethanol at 30℃; for 12h; pH=7.2; aq. phosphate buffer; optical yield given as %ee; enantioselective reaction;
3-chloropropiophenone
936-59-4

3-chloropropiophenone

A

(S)-1-phenyl-1-propanol
613-87-6

(S)-1-phenyl-1-propanol

B

3-chloro-1-phenylpropanol
100306-34-1

3-chloro-1-phenylpropanol

C

(1R)-3-chloro-1-phenylpropanol
100306-33-0

(1R)-3-chloro-1-phenylpropanol

D

1-phenyl-propan-1-one
93-55-0

1-phenyl-propan-1-one

Conditions
ConditionsYield
With yeast strain Aureobasidium pullulans CQA at 28℃; for 48h; Microbiological reaction; Enzymatic reaction;A n/a
B n/a
C n/a
D n/a
With yeast culture of Candida viswanathii KCh 120 In acetone at 25℃; for 6h; Microbiological reaction; enantioselective reaction;A 30 %Chromat.
B n/a
C n/a
D 23 %Chromat.
3-chloropropiophenone
936-59-4

3-chloropropiophenone

A

(R)-1-phenyl-1-propanol
1565-74-8

(R)-1-phenyl-1-propanol

B

(S)-1-phenyl-1-propanol
613-87-6

(S)-1-phenyl-1-propanol

C

3-chloro-1-phenylpropanol
100306-34-1

3-chloro-1-phenylpropanol

D

(1R)-3-chloro-1-phenylpropanol
100306-33-0

(1R)-3-chloro-1-phenylpropanol

E

1-phenyl-propan-1-one
93-55-0

1-phenyl-propan-1-one

Conditions
ConditionsYield
With yeast culture of Aphanocladium album KCh 417 In acetone at 25℃; for 144h; Microbiological reaction; enantioselective reaction;A n/a
B n/a
C n/a
D n/a
E 21 %Chromat.
With yeast culture of Saccharomyces cerevisiae KCh 464 In acetone at 25℃; for 144h; Microbiological reaction; enantioselective reaction;A n/a
B n/a
C n/a
D n/a
E 33 %Chromat.
With yeast culture of Saccharomyces pastorianus KCh 906 In acetone at 25℃; for 24h; Reagent/catalyst; Microbiological reaction; enantioselective reaction;A n/a
B n/a
C n/a
D n/a
E 33 %Chromat.
3-chloropropiophenone
936-59-4

3-chloropropiophenone

A

(R)-1-phenyl-1-propanol
1565-74-8

(R)-1-phenyl-1-propanol

B

3-chloro-1-phenylpropanol
100306-34-1

3-chloro-1-phenylpropanol

C

(1R)-3-chloro-1-phenylpropanol
100306-33-0

(1R)-3-chloro-1-phenylpropanol

D

1-phenyl-propan-1-one
93-55-0

1-phenyl-propan-1-one

Conditions
ConditionsYield
With yeast culture of Candida parapsilosis KCh 909 In acetone at 25℃; for 72h; Microbiological reaction; enantioselective reaction;A 29 %Chromat.
B n/a
C n/a
D 33 %Chromat.
With yeast culture of Candida viswanathii KCh 120 In acetone at 25℃; for 144h; Microbiological reaction; enantioselective reaction;A 28 %Chromat.
B n/a
C n/a
D 57 %Chromat.
3-chloropropiophenone
936-59-4

3-chloropropiophenone

A

3-chloro-1-phenylpropanol
100306-34-1

3-chloro-1-phenylpropanol

B

(1R)-3-chloro-1-phenylpropanol
100306-33-0

(1R)-3-chloro-1-phenylpropanol

C

1-phenyl-propan-1-one
93-55-0

1-phenyl-propan-1-one

Conditions
ConditionsYield
With yeast culture of Saccharomyces brasiliensis KCh 905 In acetone at 25℃; for 24h; Microbiological reaction; enantioselective reaction;A n/a
B n/a
C 61 %Chromat.
C15H22BClO3

C15H22BClO3

(1R)-3-chloro-1-phenylpropanol
100306-33-0

(1R)-3-chloro-1-phenylpropanol

Conditions
ConditionsYield
With silica gel In toluene at 20℃; for 1h; Schlenk technique; Glovebox;
(1R)-3-chloro-1-phenylpropanol
100306-33-0

(1R)-3-chloro-1-phenylpropanol

NaI

NaI

(R)-3-iodo-1-phenyl-1-propanol
127073-84-1

(R)-3-iodo-1-phenyl-1-propanol

Conditions
ConditionsYield
In acetone for 16h; Heating;99%
(1R)-3-chloro-1-phenylpropanol
100306-33-0

(1R)-3-chloro-1-phenylpropanol

(R)-3-iodo-1-phenyl-1-propanol
127073-84-1

(R)-3-iodo-1-phenyl-1-propanol

Conditions
ConditionsYield
With sodium iodide In acetone for 16h; Reflux; enantioselective reaction;99%
With sodium iodide In acetone for 16h; Finkelstein Reaction; Heating / reflux;98%
With sodium iodide In acetone for 16h; Reflux;91%
With sodium iodide
With sodium iodide In acetone
(1R)-3-chloro-1-phenylpropanol
100306-33-0

(1R)-3-chloro-1-phenylpropanol

(R)-α-(2-azidoethyl)benzenemethanol
168465-69-8

(R)-α-(2-azidoethyl)benzenemethanol

Conditions
ConditionsYield
With sodium azide In N,N-dimethyl-formamide at 25℃; for 18h;99%
With sodium azide99%
In dimethyl sulfoxide79%
With sodium azide In dimethyl sulfoxide at 40℃; for 1.5h;79%
Multi-step reaction with 2 steps
1: NaI
2: NaN3
View Scheme
4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

(1R)-3-chloro-1-phenylpropanol
100306-33-0

(1R)-3-chloro-1-phenylpropanol

(R)-4-(3-hydroxy-3-phenylpropoxy)benzaldehyde

(R)-4-(3-hydroxy-3-phenylpropoxy)benzaldehyde

Conditions
ConditionsYield
Stage #1: 4-hydroxy-benzaldehyde With caesium carbonate In tetrahydrofuran; N,N-dimethyl-formamide at 50℃; for 1h;
Stage #2: (1R)-3-chloro-1-phenylpropanol In tetrahydrofuran; N,N-dimethyl-formamide at 50℃; for 16h; Inert atmosphere;
95%
With potassium carbonate In tetrahydrofuran; N,N-dimethyl-formamide at 50℃;
2-methyl-N-[3-(4-piperidinyl)phenyl]propanamide
387827-32-9

2-methyl-N-[3-(4-piperidinyl)phenyl]propanamide

(1R)-3-chloro-1-phenylpropanol
100306-33-0

(1R)-3-chloro-1-phenylpropanol

N-(3-{1-[(3R)-3-HYDROXY-3-PHENYLPROPYL]-4-PIPERIDINYL}PHENYL)-2-METHYLPROPANAMIDE
387826-71-3

N-(3-{1-[(3R)-3-HYDROXY-3-PHENYLPROPYL]-4-PIPERIDINYL}PHENYL)-2-METHYLPROPANAMIDE

Conditions
ConditionsYield
With potassium carbonate; sodium iodide In DMF (N,N-dimethyl-formamide) at 100℃; for 3h;94.3%
With N-ethyl-N,N-diisopropylamine; tetra-(n-butyl)ammonium iodide In 1,4-dioxane34.2%
With N-ethyl-N,N-diisopropylamine; tetra-(n-butyl)ammonium iodide In 1,4-dioxane34.2%
With N-ethyl-N,N-diisopropylamine; tetra-(n-butyl)ammonium iodide In 1,4-dioxane at 90℃; for 72h;34.2%
3-Iodophenol
626-02-8

3-Iodophenol

(1R)-3-chloro-1-phenylpropanol
100306-33-0

(1R)-3-chloro-1-phenylpropanol

(R)-1-(3-chloro-1-phenylpropoxy)-3-iodobenzene

(R)-1-(3-chloro-1-phenylpropoxy)-3-iodobenzene

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 20h; Mitsunobu Displacement;89%
(1R)-3-chloro-1-phenylpropanol
100306-33-0

(1R)-3-chloro-1-phenylpropanol

(Z)-diphenyl[(Z)-2-phenyl-2-(phenylsulfonyl)vinyl]selenonium trifluoromethanesulfonate

(Z)-diphenyl[(Z)-2-phenyl-2-(phenylsulfonyl)vinyl]selenonium trifluoromethanesulfonate

(Z)-β-[(1R)-3-chloro-1-phenylpropoxy]-α-(phenylsulfonyl)styrene

(Z)-β-[(1R)-3-chloro-1-phenylpropoxy]-α-(phenylsulfonyl)styrene

Conditions
ConditionsYield
With sodium hydride In acetonitrile at -30℃; for 2h; Substitution;88%
3-(4-hydroxynaphthalen-1-yl)-1-phenylpropan-1-one

3-(4-hydroxynaphthalen-1-yl)-1-phenylpropan-1-one

(1R)-3-chloro-1-phenylpropanol
100306-33-0

(1R)-3-chloro-1-phenylpropanol

C28H26O3

C28H26O3

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 70℃; for 5h;87%
(1R)-3-chloro-1-phenylpropanol
100306-33-0

(1R)-3-chloro-1-phenylpropanol

(R)-(+)-2-Phenyloxetane
106760-61-6

(R)-(+)-2-Phenyloxetane

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran at 25℃; for 4h;86%
With potassium tert-butylate In tetrahydrofuran for 4h;82%
With potassium tert-butylate In tetrahydrofuran at 20℃; for 12h; Schlenk technique; Glovebox; enantioselective reaction;81%
With potassium hydride In tetrahydrofuran at 0 - 20℃; for 15h;76%
With potassium tert-butylate In tetrahydrofuran
morpholine
110-91-8

morpholine

(1R)-3-chloro-1-phenylpropanol
100306-33-0

(1R)-3-chloro-1-phenylpropanol

(R)-3-morpholino-1-phenylpropan-1-ol
40116-81-2

(R)-3-morpholino-1-phenylpropan-1-ol

Conditions
ConditionsYield
at 80℃;86%
at 80℃;
α-naphthol
90-15-3

α-naphthol

(1R)-3-chloro-1-phenylpropanol
100306-33-0

(1R)-3-chloro-1-phenylpropanol

(R)-(-)-3-(1-naphthalenyloxy)-1-phenyl-1-propanol

(R)-(-)-3-(1-naphthalenyloxy)-1-phenyl-1-propanol

Conditions
ConditionsYield
With sodium hydroxide In N,N-dimethyl acetamide at 60 - 80℃;85.6%
Stage #1: α-naphthol With sodium hydride In N,N-dimethyl-formamide for 1h; Cooling with ice;
Stage #2: (1R)-3-chloro-1-phenylpropanol In N,N-dimethyl-formamide for 1h; Cooling with ice;
74%
With sodium hydroxide In water; N,N-dimethyl-formamide; toluene at 90 - 95℃; for 2h; Large scale reaction;67.2%
With potassium hydroxide In acetone at 0℃; Inert atmosphere; Reflux;
2-bromo-p-cresol
6627-55-0

2-bromo-p-cresol

(1R)-3-chloro-1-phenylpropanol
100306-33-0

(1R)-3-chloro-1-phenylpropanol

(S)-2-bromo-1-(3-chloro-1-phenylpropoxy)-4-methyl-benzene

(S)-2-bromo-1-(3-chloro-1-phenylpropoxy)-4-methyl-benzene

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; Mitsunobu reaction;82%
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; Mitsunobu reaction;82%
tert-Butyl N-hydroxycarbamate
36016-38-3

tert-Butyl N-hydroxycarbamate

(1R)-3-chloro-1-phenylpropanol
100306-33-0

(1R)-3-chloro-1-phenylpropanol

tert-butyl N-[(3R)-3-hydroxy-3-phenylpropoxy]carbamate

tert-butyl N-[(3R)-3-hydroxy-3-phenylpropoxy]carbamate

Conditions
ConditionsYield
Stage #1: tert-Butyl N-hydroxycarbamate With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.333333h; Inert atmosphere;
Stage #2: (1R)-3-chloro-1-phenylpropanol In N,N-dimethyl-formamide at 0 - 20℃; for 72h; Inert atmosphere;
82%
Stage #1: tert-Butyl N-hydroxycarbamate With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h;
Stage #2: (1R)-3-chloro-1-phenylpropanol In N,N-dimethyl-formamide at 0 - 20℃; for 72h;
68%
Stage #1: tert-Butyl N-hydroxycarbamate With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h;
Stage #2: (1R)-3-chloro-1-phenylpropanol In N,N-dimethyl-formamide at 0 - 20℃; for 72h;
2-bromo-4-chlorophenol
695-96-5

2-bromo-4-chlorophenol

(1R)-3-chloro-1-phenylpropanol
100306-33-0

(1R)-3-chloro-1-phenylpropanol

(S)-2-bromo-4-chloro-1-(3-chloro-1-phenylpropoxy)-benzene

(S)-2-bromo-4-chloro-1-(3-chloro-1-phenylpropoxy)-benzene

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; Mitsunobu reaction;81%
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; Mitsunobu reaction;81%
2,4-dibromophenol
615-58-7

2,4-dibromophenol

(1R)-3-chloro-1-phenylpropanol
100306-33-0

(1R)-3-chloro-1-phenylpropanol

(S)-2,4-dibromo-1-(3-chloro-1-phenylpropoxy)-benzene
319924-81-7

(S)-2,4-dibromo-1-(3-chloro-1-phenylpropoxy)-benzene

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; Mitsunobu reaction;79%
2-hydroxybromobenzene
95-56-7

2-hydroxybromobenzene

(1R)-3-chloro-1-phenylpropanol
100306-33-0

(1R)-3-chloro-1-phenylpropanol

(S)-1-bromo-2-(3-chloro-1-phenylpropoxy)-benzene
319924-80-6

(S)-1-bromo-2-(3-chloro-1-phenylpropoxy)-benzene

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; Mitsunobu reaction;78%
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; Mitsunobu reaction;78%
2,6-dibromophenol
608-33-3

2,6-dibromophenol

(1R)-3-chloro-1-phenylpropanol
100306-33-0

(1R)-3-chloro-1-phenylpropanol

(S)-2,6-dibromo-1-(3-chloro-1-phenylpropoxy)-benzene
319924-93-1

(S)-2,6-dibromo-1-(3-chloro-1-phenylpropoxy)-benzene

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; Mitsunobu reaction;77%
2-bromo-3,5-dimethoxyphenol
121449-70-5

2-bromo-3,5-dimethoxyphenol

(1R)-3-chloro-1-phenylpropanol
100306-33-0

(1R)-3-chloro-1-phenylpropanol

(S)-2-bromo-1-(3-chloro-1-phenylpropoxy)-3,5-dimethoxy-benzene

(S)-2-bromo-1-(3-chloro-1-phenylpropoxy)-3,5-dimethoxy-benzene

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; Mitsunobu reaction;76%
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; Mitsunobu reaction;76%
3-Hydroxyacetophenone
121-71-1

3-Hydroxyacetophenone

(1R)-3-chloro-1-phenylpropanol
100306-33-0

(1R)-3-chloro-1-phenylpropanol

1-(3-{[(1S)-3-chloro-1-phenylpropyl]oxy}phenyl)ethanone
487058-12-8

1-(3-{[(1S)-3-chloro-1-phenylpropyl]oxy}phenyl)ethanone

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran76%
4-Phenoxyphenol
831-82-3

4-Phenoxyphenol

(1R)-3-chloro-1-phenylpropanol
100306-33-0

(1R)-3-chloro-1-phenylpropanol

4-{[(1S)-3-chloro-1-phenylpropyl]oxy}-(4-phenoxy)benzene
387827-50-1

4-{[(1S)-3-chloro-1-phenylpropyl]oxy}-(4-phenoxy)benzene

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; for 24h;75.7%
(1R)-3-chloro-1-phenylpropanol
100306-33-0

(1R)-3-chloro-1-phenylpropanol

benzylamine
100-46-9

benzylamine

(R)-3-(benzylamino)-1-phenylpropan-1-ol
185376-75-4

(R)-3-(benzylamino)-1-phenylpropan-1-ol

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In acetonitrile at 75℃; for 48h;75%
phthalimide
136918-14-4

phthalimide

(1R)-3-chloro-1-phenylpropanol
100306-33-0

(1R)-3-chloro-1-phenylpropanol

2-[(1S)-3-chloro-1-phenylpropyl]-1H-isoindole-1,3(2H)-dione
387827-49-8

2-[(1S)-3-chloro-1-phenylpropyl]-1H-isoindole-1,3(2H)-dione

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; for 4h;74%
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; for 24h;50.2%
phthalimide
136918-14-4

phthalimide

(1R)-3-chloro-1-phenylpropanol
100306-33-0

(1R)-3-chloro-1-phenylpropanol

diethylazodicarboxylate
1972-28-7

diethylazodicarboxylate

2-[(1S)-3-chloro-1-phenylpropyl]-1H-isoindole-1,3(2H)-dione
387827-49-8

2-[(1S)-3-chloro-1-phenylpropyl]-1H-isoindole-1,3(2H)-dione

Conditions
ConditionsYield
With triphenylphosphine In tetrahydrofuran; hexane; ethyl acetate74%
(1R)-3-chloro-1-phenylpropanol
100306-33-0

(1R)-3-chloro-1-phenylpropanol

methylamine
74-89-5

methylamine

(R)-N-methyl-3-phenyl-3-hydroxypropylamine
115290-81-8

(R)-N-methyl-3-phenyl-3-hydroxypropylamine

Conditions
ConditionsYield
With potassium iodide In methanol; water at 80℃; for 8h;72%
With sodium iodide In water
ortho-cresol
95-48-7

ortho-cresol

(1R)-3-chloro-1-phenylpropanol
100306-33-0

(1R)-3-chloro-1-phenylpropanol

-(+)-1-chloro-3-phenyl-3-(2-methylphenoxy)propane
114446-50-3

-(+)-1-chloro-3-phenyl-3-(2-methylphenoxy)propane

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran Ambient temperature;68%
With triphenylphosphine; diethylazodicarboxylate In diethyl ether
With triphenylphosphine; diethylazodicarboxylate
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran Ambient temperature;
4-hydroxybenzotrifluoride
402-45-9

4-hydroxybenzotrifluoride

(1R)-3-chloro-1-phenylpropanol
100306-33-0

(1R)-3-chloro-1-phenylpropanol

-(-)-1-chloro-3-phenyl-3-<4-(trifluoromethyl)phenoxy>propane
114446-51-4

-(-)-1-chloro-3-phenyl-3-<4-(trifluoromethyl)phenoxy>propane

Conditions
ConditionsYield
Stage #1: 4-hydroxybenzotrifluoride With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 4h; Mitsunobu reaction; Inert atmosphere;
Stage #2: (1R)-3-chloro-1-phenylpropanol In tetrahydrofuran at 20℃; Mitsunobu reaction; Inert atmosphere;
66%
With triphenylphosphine; diethylazodicarboxylate
(1R)-3-chloro-1-phenylpropanol
100306-33-0

(1R)-3-chloro-1-phenylpropanol

α,α,α-trifluoro-p-cresol
402-45-9

α,α,α-trifluoro-p-cresol

-(-)-1-chloro-3-phenyl-3-<4-(trifluoromethyl)phenoxy>propane
114446-51-4

-(-)-1-chloro-3-phenyl-3-<4-(trifluoromethyl)phenoxy>propane

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran Ambient temperature;65%
(1R)-3-chloro-1-phenylpropanol
100306-33-0

(1R)-3-chloro-1-phenylpropanol

2-bromo-5,6,7,8-tetrahydronaphthalen-1-ol
319924-91-9

2-bromo-5,6,7,8-tetrahydronaphthalen-1-ol

6-Bromo-5-((S)-3-chloro-1-phenyl-propoxy)-1,2,3,4-tetrahydro-naphthalene

6-Bromo-5-((S)-3-chloro-1-phenyl-propoxy)-1,2,3,4-tetrahydro-naphthalene

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; Mitsunobu reaction;64%

100306-33-0Relevant articles and documents

Identification of key residues in Debaryomyces hansenii carbonyl reductase for highly productive preparation of (S)-aryl halohydrins

Xu, Guo-Chao,Shang, Yue-Peng,Yu, Hui-Lei,Xu, Jian-He

, p. 15728 - 15731 (2015)

Key residues of Debaryomyces hansenii carbonyl reductase in the determination of the reducing activity towards aryl haloketones were identified through combinatorial mutation of conserved residues. This study provides a green and efficient biocatalyst for the synthesis of (S)-aryl halohydrins.

PEG600-carboxylates as efficient reusable reaction media and acylating agents for the resolution of sec-alcohols

Monteiro, Carlos M.,Lourenco, Nuno M. T.,Ferreira, Frederico C.,Afonso, Carlos A. M.

, p. 42 - 46 (2015)

Herein is presented a simple, attractive, and reusable methodology for one-pot resolution/separation of free sec-alcohols with enantiomeric excess (ee) values over 90% by the combination of sustainable acylating agents/solvents (polyethylene glycol derivatives) and an easily available and common biocatalyst (Candida antarctica lipase B, or CAL B) under irreversible conditions, along with a separation process by extraction or distillation. A scale-up reaction was carried out with the Fluoxetine precursor with ee values close to 90% for the R enantiomer.

A new catalytic enantioselective reducing reagent system from (-)-α,α-diphenylpyrrolidinemethanol and 9-borabicyclo[3.3.1]nonane, especially effective for hindered and substituted aralkylketones

Kanth, Josyula V.B.,Brown, Herbert C.

, p. 1069 - 1074 (2002)

New catalytic enantioselective reduction systems were prepared from aminoalcohols and dialkylboranes, for the enantioselective reductions of prochiral aromatic ketones. Among these, the system prepared from (-)-α,α-diphenylpyrrolidinemethanol with 9-borabicyclo[3.3.1]nonane proved especially promising for such reductions. This complex catalyzes the reduction of prochiral aralkyl ketones to the corresponding alcohols with BH3-THF, with enantioselectivities 82-99.2%. Also, this catalyst is particularly effective for the more hindered and substituted aralkyl ketones. Various modifications in this new catalytic reduction system, such as changing reaction conditions, reducing agent and dialkylborane, were also examined.

Pen G acylase catalyzed resolution of phenylacetate esters of secondary alcohols

Baldaro,D'Arrigo,Pedrocchi-Fantoni,Rosell,Tagliani,Terreni,Servi

, p. 1031 - 1034 (1993)

Penicillin G acylase from E. coli (E.C. 3.5.1.11) immobilized on Eupergit C is used for the kinetic resolution of phenyl acetate esters of secondary alcohols of pharmaceutical interest.

Chemoenzymatic synthesis of fluoxetine precursors. Reduction of β-substituted propiophenones

Coronel, Camila,Arce, Gabriel,Iglesias, Cesar,Noguera, Cynthia Magallanes,Bonnecarrere, Paula Rodriguez,Giordano, Sonia Rodriguez,Gonzalez, David

, p. 94 - 98 (2014)

Five endophytic yeast strains isolated from edible plants were tested in the reduction β-chloro- and β-azidopropiophenone for the preparation of optically active fluoxetine precursors. The biotransformation rendered not only the corresponding chiral γ-substituted alcohols, but also unsubstituted alcohols and ketones. The product profile was studied and a plausible mechanism for the reductive elimination of the β-functional group is proposed.

Asymmetric Synthesis of 2-Aryl Substituted Oxetanes by Enantioselective Reduction of β-Halogenoketones using Lithium Borohydride modified with N,N'-Dibenzoylcystine

Soai, Kenso,Niwa, Seiji,Yamanoi, Takashi,Hikima, Hitoshi,Ishizaki, Miyuki

, p. 1018 - 1019 (1986)

Optically active 2-aryl substituted oxetanes are synthesised in high enantiomeric excesses (up to 89percent e.e.) via enantioselective reduction of β-halogenoketones with lithium borohydride using (R,R')-N,N'-dibenzoylcystine and t-butyl alcohols as ligands.

Facile access to chiral alcohols with pharmaceutical relevance using a ketoreductase newly mined from Pichia guilliermondii

Xu, Guochao,Yu, Huilei,Xu, Jianhe

, p. 349 - 354 (2013)

Chiral secondary alcohols with additional functional groups are frequently required as important and valuable synthons for pharmaceuticals, agricultural and other fine chemicals. With the advantages of environmentally benign reaction conditions, broad reaction scope, and high stereoselectivity, biocatalytic reduction of prochiral ketones offers significant potential in the synthesis of optically active alcohols. A CmCR homologous carbonyl reductase from Pichia guilliermondii NRRL Y-324 was successfully overexpressed. Substrate profile characterization revealed its broad substrate specificity, covering aryl ketones, aliphatic ketones and ketoesters. Furthermore, a variety of ketone substrates were asymmetrically reduced by the purified enzyme with an additionally NADPH regeneration system. The reduction system exhibited excellent enantioselectivity (>99% ee) in the reduction of all the aromatic ketones and ketoesters, except for 2-bromoacetophenone (93.5% ee). Semi-preparative reduction of six ketones was achieved with high enantioselectivity (>99% ee) and isolation yields (>80%) within 12 h. This study provides a useful guidance for further application of this enzyme in the asymmetric synthesis of chiral alcohol enantiomers. Copyright

Chiral N-heterocyclic carbene iridium catalyst for the enantioselective hydrosilane reduction of ketones

Manabe, Yoshiki,Shinohara, Kanako,Nakamura, Hanako,Teramoto, Hiro,Sakaguchi, Satoshi

, p. 138 - 145 (2016)

Enantioselective reduction of ketones with (EtO)2MeSiH catalyzed by an in-situ generated N-heterocyclic carbene (NHC) Ir complex at room temperature has been developed. A series of benzimidazolium salts were synthesized and screened in the asymmetric hydrosilylation reaction. As a result, propiophenone was efficiently reduced by the combined catalytic system of [IrCl(cod)]2 and NHC-Ag complex derived from N-(1-naphthalenylmethyl)-substituted benzimidazolium salt L12, affording the corresponding alcohol in 92% yield and with 92% ee. Moreover, the evaluation of an Ir catalyst precursor showed that cationic [Ir(cod)2]BF4 complex could be used. Furthermore, the introduction of a chiral hydroxyamide side arm into the benzimidazolium salt was critical for the successful design of the NHC ligand.

Diphenyloxazaborolidine a new catalyst for enantioselective reduction of ketones

Quallich, George J.,Woodall, Teresa M.

, p. 4145 - 4148 (1993)

A variety of ketones can be reduced in high enantioselectivity with the oxazaborolidines derived from commercially available erythro aminodiphenylethanol.

Ultrafast Iron-Catalyzed Reduction of Functionalized Ketones: Highly Enantioselective Synthesis of Halohydrines, Oxaheterocycles, and Aminoalcohols

Blasius, Clemens K.,Vasilenko, Vladislav,Gade, Lutz H.

, p. 10231 - 10235 (2018)

A molecularly defined chiral boxmi iron alkyl complex catalyzes the hydroboration of various functionalized ketones and provides the corresponding chiral halohydrines, oxaheterocycles (oxiranes, oxetanes, tetrahydrofurans, and dioxanes) and amino alcohols with excellent enantioselectivities (up to >99 %ee) and conversion efficiencies at low catalyst loadings (as low as 0.5 mol %). Turnover frequencies of greater than 40000 h?1 at ?30 °C highlight the activity of this earth-abundant metal catalyst which tolerates a large number of functional groups.

Asymmetric reduction of prochiral ketones using in situ generated oxazaborolidine derived from (1S,2S,3R,4R)-3-amino-7,7-dimethoxynorbornan-2-ol. An efficient synthesis of enantiopure (R)-tomoxetine

Lapis, Alexandre A. M.,De Fátima, ?ngelo,Martins, José E. D.,Costa, Valentim E. U.,Pilli, Ronaldo A.

, p. 495 - 498 (2005)

In this work, we report our results on the asymmetric reduction of prochiral aromatic and aliphatic ketones 3, 5-8 catalyzed by the novel in situ generated oxazaborolidine 2 derived from (1S,2S,3R,4R)-3-amino-7,7- dimethoxybornan-2-ol (1) and BH3?Me2S. This methodology was applied to the synthesis of the anti-depressant drug (R)-tomoxetine in three steps and 47% overall yield from 3-chloropropiophenone (3h). Catalytic asymmetric reduction of prochiral ketones was examined in the presence of chiral oxazaborolidine catalyst 2 prepared in situ from (1S,2S,3R,4R)-3-amino-7,7-dimethoxynorbornan-2-ol (1). The optically active secondary alcohols were generally obtained in moderate to high enantiomeric excesses (ee 43-95%) and good yields (75-94%), except for ketones bearing electron-withdrawing groups. The methodology was applied to the synthesis of enantiopure (R)-tomoxetine, a potent anti-depressant drug.

Total Synthesis of Meayamycin B

Basu, Upamanyu,Bressin, Robert K.,Koide, Kazunori,Osman, Sami,Pohorilets, Ivanna

supporting information, p. 4637 - 4647 (2020/05/01)

Meayamycin B is currently the most potent modulator of the splicing factor 3b subunit 1 and used by dozens of research groups. However, current supply for this natural product analogue is limited because of the lengthy synthetic scheme. Here, we report a more concise, more cost-effective, and greener synthesis of this compound by developing and employing a novel asymmetric reduction of a prochiral enone to afford an allylic alcohol with high enantioselectivity. In addition to this reaction, this synthesis highlights a scalable Mukaiyama aldol reaction, Nicolaou-type epoxide opening reaction, stereoselective Corey-Chaykovsky-type reaction, and a modified Horner-Wadsworth-Emmons Z-selective olefination. We also discuss a Z-E isomerization during the α,β-unsaturated amide formation. The new synthesis of meayamycin B consists of 11 steps in the longest linear sequence and 24 total steps.

Iridium-Catalyzed Asymmetric Hydrogenation of Halogenated Ketones for the Efficient Construction of Chiral Halohydrins

Yin, Congcong,Wu, Weilong,Hu, Yang,Tan, Xuefeng,You, Cai,Liu, Yuanhua,Chen, Ziyi,Dong, Xiu-Qin,Zhang, Xumu

supporting information, p. 2119 - 2124 (2018/04/30)

Iridium-catalyzed asymmetric hydrogenation of prochiral halogenated ketones was successfully developed to prepare various chiral halohydrins with high reactivities and excellent enantioselectivities under basic reaction condition (up to >99% conversion, 99% yield, >99% ee). Moreover, gram-scale experiment was performed well in the presence of just 0.005 mol% (S/C=20 000) Ir/f-amphox catalyst with 99% yield and >99% ee. (Figure presented.).

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