Welcome to LookChem.com Sign In|Join Free

CAS

  • or

56553-60-7

Post Buying Request

56553-60-7 Suppliers

Recommended suppliersmore

  • Product
  • FOB Price
  • Min.Order
  • Supply Ability
  • Supplier
  • Contact Supplier

56553-60-7 Usage

Chemical Description

Sodium triacetoxyborohydride is a reducing agent used in organic synthesis.

Chemical Properties

Sodium triacetoxyborohydride (STAB-H) is commercially available as a hygroscopic white powder with a melting point of 116-120 °C. freely soluble in benzene. It is prepared by the reaction of NaBH4 with excess acetic acid in benzene or toluene.

Uses

Sodium Triacetoxyborohydride(STAB) is a hydride reagent used in stereoselective reductive amination. It is able to replace toxic sodium cyanoborohydride under most conditions. It is selective in reducing aldehydes to alcohols in the presence of ketones. STAB is also stable in anhydrous acids, which enables reductive amination of aldehydes and ketones. It used in reductive amination of ketones and aldehydes and reductive amination/lactamization of carbonyl compounds with amines. The advantage of STAB compared to sodium cyanoborohydride is evident. STAB, being non-toxic, is easier to handle and forms no toxic by-products, making the treatment of process waste after the reaction simple and less costly.

Application

Sodium triacetoxyborohydride is a mild reagent that exhibits remarkable selectivity as a reducing agent. It reduces aldehydes but not ketones; however, beta-hydroxyketones can be reduced selectively to give 1,3-trans diols.The steric and the electron-withdrawing effects of the three acetoxy groups stabilize the boron-hydrogen bond and are responsible for its mild reducing properties.Sodium triacetoxyborohydride or [NaBH(OAc)3] can be used as a reagent:In the reductive amination of ketones and aldehydes.To prepare N-benzyl-γ-valerolactam by reacting with methyl 4-oxopentanoate and benzylamine via reductive amination/lactamization.To reduce imines and enamines to corresponding amines.To reduce quinolines and isoquinolines to corresponding tetrahydro derivatives.In the hydroboration of alkenes.To synthesize nitroxide biradicals for creating high relaxivity terminal groups linkage to dendrimers.

Reactions

Sodium Triacetoxyborohydride is selective reducing agent in organic synthesis. It is especially suitable for reductive aminations. Since the reaction rate for the reduction of iminium ions is much faster than for ketones or even aldehydes, the reductive amination can be carried out as a one-pot procedure by introducing the reducing agent into a mixture of the amine and carbonyl compound. The presence of a stoichiometric amount of acetic acid, which catalyzes the imine formation and provides the iminium ion, doesn't present any problem under these conditions.Reductive amination (simplified)

Check Digit Verification of cas no

The CAS Registry Mumber 56553-60-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,6,5,5 and 3 respectively; the second part has 2 digits, 6 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 56553-60:
(7*5)+(6*6)+(5*5)+(4*5)+(3*3)+(2*6)+(1*0)=137
137 % 10 = 7
So 56553-60-7 is a valid CAS Registry Number.
InChI:InChI=1/C6H10BO6.Na/c1-11-4(8)7(5(9)12-2)6(10)13-3;/h7H,1-3H3;/q-1;+1/rC6H10BNaO6/c1-12-4(9)7(8,5(10)13-2)6(11)14-3/h7H,1-3H3

56553-60-7 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (S0394)  Sodium Triacetoxyborohydride  >80.0%(T)

  • 56553-60-7

  • 25g

  • 390.00CNY

  • Detail
  • TCI America

  • (S0394)  Sodium Triacetoxyborohydride  >80.0%(T)

  • 56553-60-7

  • 100g

  • 990.00CNY

  • Detail
  • Alfa Aesar

  • (B22060)  Sodium triacetoxyborohydride, 95%   

  • 56553-60-7

  • 5g

  • 150.0CNY

  • Detail
  • Alfa Aesar

  • (B22060)  Sodium triacetoxyborohydride, 95%   

  • 56553-60-7

  • 25g

  • 404.0CNY

  • Detail
  • Alfa Aesar

  • (B22060)  Sodium triacetoxyborohydride, 95%   

  • 56553-60-7

  • 100g

  • 1186.0CNY

  • Detail
  • Aldrich

  • (316393)  Sodiumtriacetoxyborohydride  97%

  • 56553-60-7

  • 316393-25G

  • 460.98CNY

  • Detail
  • Aldrich

  • (316393)  Sodiumtriacetoxyborohydride  97%

  • 56553-60-7

  • 316393-100G

  • 1,385.28CNY

  • Detail
  • Aldrich

  • (316393)  Sodiumtriacetoxyborohydride  97%

  • 56553-60-7

  • 316393-500G

  • 5,496.66CNY

  • Detail

56553-60-7SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Sodium Triacetoxyborohydride

1.2 Other means of identification

Product number -
Other names sodium,triacetyloxyboron(1-)

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:56553-60-7 SDS

56553-60-7Synthetic route

sodium tetrahydroborate
16940-66-2

sodium tetrahydroborate

sodium tris(acetoxy)borohydride
56553-60-7

sodium tris(acetoxy)borohydride

Conditions
ConditionsYield
With acetic acid In benzene byproducts: H2; under N2-atmosphere; slurry of NaBH4 in benzene cooled (10°C); CH3COOH added dropwise (temp. < 20°C); mixt. warmed (ambient temp.) and stirred for 8h;; filtration; white powder washed (ether) and held under vacuum over night; elem. anal.;;92%
acetic acid
64-19-7

acetic acid

sodium tris(acetoxy)borohydride
56553-60-7

sodium tris(acetoxy)borohydride

Conditions
ConditionsYield
With sodium tetrahydroborate In benzene
With sodium tetrahydroborate at 15 - 20℃;
With sodium tetrahydroborate In 2-methylpropyl acetate at 0 - 5℃; for 1h;
With sodium tetrahydroborate In dichloromethane for 2h;
With sodium tetrahydroborate In tetrahydrofuran at 0 - 20℃; Inert atmosphere; Schlenk technique;
sodium triacetoxyborohydride

sodium triacetoxyborohydride

acetic acid
64-19-7

acetic acid

sodium tris(acetoxy)borohydride
56553-60-7

sodium tris(acetoxy)borohydride

triacetoxyborane
4887-24-5

triacetoxyborane

sodium hydride
7646-69-7

sodium hydride

A

sodium triacetoxyborohydride

sodium triacetoxyborohydride

B

sodium tris(acetoxy)borohydride
56553-60-7

sodium tris(acetoxy)borohydride

Conditions
ConditionsYield
In 1,4-dioxane addn. of soln. of tris(acetoxy)borane in dry dioxane to suspension of NaH in dry dioxane; refluxing of mixt. for 4 h; Na(HB(OCOCH3)3) and small amts. of Na(H2B(OCOCH3)2) obtained;
In 1,4-dioxane boiling the mixture 4 hours long;
In 1,4-dioxane on boiling, pptn. of NaBH(OCOCH3)3, small amounts of NaBH2(OCOCH3)2 in the filtrate;;
sodium tetrahydroborate
16940-66-2

sodium tetrahydroborate

acetic acid
64-19-7

acetic acid

sodium tris(acetoxy)borohydride
56553-60-7

sodium tris(acetoxy)borohydride

Conditions
ConditionsYield
In N,N-dimethyl acetamide Kinetics; byproducts: H2; NaBH4 charged into an acetic acid/N,N-dimethylacetamide soln. at -10°C, warmed to 22°C, aged; the process studied in a calorimeterto evaluate thermal hazards;
refluxing Na with glacial acetic acid in ratio of 4:3.25 equivalents for 15 min. under N2;
refluxing Na with glacial acetic acid in ratio of 4:3.25 equivalents for 15 min. under N2;
trifluoromethanesulfonate 2-cyano-1,1,4-trimethyl-3-phenyl-azetidinium

trifluoromethanesulfonate 2-cyano-1,1,4-trimethyl-3-phenyl-azetidinium

sodium tris(acetoxy)borohydride
56553-60-7

sodium tris(acetoxy)borohydride

C15H20N2O2

C15H20N2O2

Conditions
ConditionsYield
In tetrahydrofuran for 24h; Heating;100%
Triphenylmethylamin
5824-40-8

Triphenylmethylamin

sodium tris(acetoxy)borohydride
56553-60-7

sodium tris(acetoxy)borohydride

N-triphenylmethyl-N-ethylamine
7370-34-5

N-triphenylmethyl-N-ethylamine

Conditions
ConditionsYield
In acetonitrile at 60℃; for 15h;99.9%
1-(2-phenylethyl)-4-piperidinone
39742-60-4

1-(2-phenylethyl)-4-piperidinone

3-Phenylpropan-1-amine
2038-57-5

3-Phenylpropan-1-amine

sodium tris(acetoxy)borohydride
56553-60-7

sodium tris(acetoxy)borohydride

1-(2-phenylethyl)-4-[N-(3-phenylpropyl)]-aminopiperidine

1-(2-phenylethyl)-4-[N-(3-phenylpropyl)]-aminopiperidine

Conditions
ConditionsYield
In dichloromethane; acetic acid at 25℃; for 20h;99%
ferrocenecarboxaldehyde
12093-10-6

ferrocenecarboxaldehyde

N,N-dimethylammonium chloride
506-59-2

N,N-dimethylammonium chloride

sodium tris(acetoxy)borohydride
56553-60-7

sodium tris(acetoxy)borohydride

N,N-dimethylaminomethylferrocene
1271-86-9

N,N-dimethylaminomethylferrocene

Conditions
ConditionsYield
With triethylamine In dichloromethane Fe complex reacted with HNMe2*HCl and B compd. in presence of Et3N in CH2Cl2;99%
3-methoxyazetidine hydrochloride

3-methoxyazetidine hydrochloride

benzyl 4-oxo-1-piperidinecarboxylate
19099-93-5

benzyl 4-oxo-1-piperidinecarboxylate

sodium tris(acetoxy)borohydride
56553-60-7

sodium tris(acetoxy)borohydride

C17H24N2O3

C17H24N2O3

Conditions
ConditionsYield
Stage #1: 3-methoxyazetidine hydrochloride; benzyl 4-oxo-1-piperidinecarboxylate With acetic acid In tetrahydrofuran at 20℃; for 0.666667h;
Stage #2: sodium tris(acetoxy)borohydride In tetrahydrofuran at 0 - 20℃;
99%
2,5-Dichloro-4-nitrophenylacetaldehyde

2,5-Dichloro-4-nitrophenylacetaldehyde

sodium tris(acetoxy)borohydride
56553-60-7

sodium tris(acetoxy)borohydride

2,5-Dichloro-4-(2-[4-(t-butoxycarbonyl)-1-piperazinyl]ethyl)-nitrobenzene

2,5-Dichloro-4-(2-[4-(t-butoxycarbonyl)-1-piperazinyl]ethyl)-nitrobenzene

Conditions
ConditionsYield
With acetic acid In 1-t-Butoxycarbonylpiperazine98%
tris[(2-(benzyloxy)-3-(3',5'-bis(trifluoromethyl)phenyl)-5-methyl)benzyl]amine

tris[(2-(benzyloxy)-3-(3',5'-bis(trifluoromethyl)phenyl)-5-methyl)benzyl]amine

sodium tris(acetoxy)borohydride
56553-60-7

sodium tris(acetoxy)borohydride

A

C48H33F18NO3

C48H33F18NO3

B

C48H30BF18NO3

C48H30BF18NO3

Conditions
ConditionsYield
With 5%-palladium/activated carbon; hydrogen In ethyl acetate at 20℃; under 5171.62 Torr; for 24h;A 98%
B n/a
formaldehyd
50-00-0

formaldehyd

benzyl (R)-[5-oxo-1-(2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yl)pyrrolidin-3-yl]carbamate
921751-98-6

benzyl (R)-[5-oxo-1-(2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yl)pyrrolidin-3-yl]carbamate

sodium tris(acetoxy)borohydride
56553-60-7

sodium tris(acetoxy)borohydride

benzyl (R)-[1-(3-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yl)-5-oxopyrrolidin-3-yl]carbamate
921751-99-7

benzyl (R)-[1-(3-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yl)-5-oxopyrrolidin-3-yl]carbamate

Conditions
ConditionsYield
Stage #1: formaldehyd; benzyl (R)-[5-oxo-1-(2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yl)pyrrolidin-3-yl]carbamate With acetic acid In methanol; water at 20℃; for 0.5h; pH=6; Michael Condensation;
Stage #2: sodium tris(acetoxy)borohydride In methanol; water for 1h;
96%
(R)-benzyl 3-(1-aminoethyl)azetidine-1-carboxylate

(R)-benzyl 3-(1-aminoethyl)azetidine-1-carboxylate

sodium tris(acetoxy)borohydride
56553-60-7

sodium tris(acetoxy)borohydride

2,4-Dimethoxybenzaldehyde
613-45-6

2,4-Dimethoxybenzaldehyde

(R)-benzyl 3-(1-((2,4-dimethoxybenzyl)amino)ethyl)azetidine-1-carboxylate

(R)-benzyl 3-(1-((2,4-dimethoxybenzyl)amino)ethyl)azetidine-1-carboxylate

Conditions
ConditionsYield
Stage #1: (R)-benzyl 3-(1-aminoethyl)azetidine-1-carboxylate; 2,4-Dimethoxybenzaldehyde With acetic acid In 1,2-dichloro-ethane at 30℃; for 1h;
Stage #2: sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 2h;
95.1%
(4R/S)-3-chloro-4-({4-amino-1-piperidinyl}methyl)-4-hydroxy-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one
943025-57-8

(4R/S)-3-chloro-4-({4-amino-1-piperidinyl}methyl)-4-hydroxy-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one

sodium tris(acetoxy)borohydride
56553-60-7

sodium tris(acetoxy)borohydride

(4R/S)-3-chloro-4-hydroxy-4-[(4-{[(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)methyl]amino}-1-piperidinyl)methyl]-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one monoacetate salt

(4R/S)-3-chloro-4-hydroxy-4-[(4-{[(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)methyl]amino}-1-piperidinyl)methyl]-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one monoacetate salt

Conditions
ConditionsYield
Stage #1: 3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carbaldehyde; (4R/S)-4-[(4-amino-1-piperidinyl)methyl]-3-chloro-4-hydroxy-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one In methanol; chloroform at 20℃; for 2h;
Stage #2: sodium tris(acetoxy)borohydride In methanol; chloroform for 2h;
95%
(4R/S)-3-chloro-4-({4-amino-1-piperidinyl}methyl)-4-hydroxy-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one
943025-57-8

(4R/S)-3-chloro-4-({4-amino-1-piperidinyl}methyl)-4-hydroxy-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one

sodium tris(acetoxy)borohydride
56553-60-7

sodium tris(acetoxy)borohydride

(4R/S)-3-chloro-4-hydroxy-4-({4-[([1,3]oxathiolo[5,4-c]pyridin-6-ylmethyl)amino]-1-piperidinyl}methyl)-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one monoacetate salt

(4R/S)-3-chloro-4-hydroxy-4-({4-[([1,3]oxathiolo[5,4-c]pyridin-6-ylmethyl)amino]-1-piperidinyl}methyl)-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one monoacetate salt

Conditions
ConditionsYield
Stage #1: (4R/S)-4-[(4-amino-1-piperidinyl)methyl]-3-chloro-4-hydroxy-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one; [1,3]oxathiolo[5,4-c]pyridine-6-carbaldehyde In methanol; chloroform at 20℃; for 2h;
Stage #2: sodium tris(acetoxy)borohydride In methanol; chloroform for 2h;
95%
N,N-diisopropylacetamide
759-22-8

N,N-diisopropylacetamide

5-methylsulfonylisoindoline hydrochloride

5-methylsulfonylisoindoline hydrochloride

sodium tris(acetoxy)borohydride
56553-60-7

sodium tris(acetoxy)borohydride

tert-butyl (2R,3S,5R)-5-(5-methylsulfonylisoindolin-2-yl)-2-(2,5-difluorophenyl)tetrahydro-2H-pyran-3-ylcarbamate

tert-butyl (2R,3S,5R)-5-(5-methylsulfonylisoindolin-2-yl)-2-(2,5-difluorophenyl)tetrahydro-2H-pyran-3-ylcarbamate

Conditions
ConditionsYield
With acetic acid95%
sodium tris(acetoxy)borohydride
56553-60-7

sodium tris(acetoxy)borohydride

1-aminooctadecane
124-30-1

1-aminooctadecane

diethyl-octadecyl-amine
30427-51-1

diethyl-octadecyl-amine

Conditions
ConditionsYield
In acetonitrile at 60℃; for 15h;94.6%
N-methyliminodiacetyl (1-(4-fluorophenyl)-2-oxoethyl)boronate
1329422-57-2

N-methyliminodiacetyl (1-(4-fluorophenyl)-2-oxoethyl)boronate

sodium tris(acetoxy)borohydride
56553-60-7

sodium tris(acetoxy)borohydride

C13H15BFNO5

C13H15BFNO5

Conditions
ConditionsYield
Stage #1: N-methyliminodiacetyl (1-(4-fluorophenyl)-2-oxoethyl)boronate With acetic acid In 1,2-dichloro-ethane for 0.166667h; Cooling with ice;
Stage #2: sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane for 5h; Cooling with ice;
94%
ferrocenecarboxaldehyde
12093-10-6

ferrocenecarboxaldehyde

sodium tris(acetoxy)borohydride
56553-60-7

sodium tris(acetoxy)borohydride

benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

N-benzyl-N-(ferrocenylmethyl)methylamine*0.1H2CO3

N-benzyl-N-(ferrocenylmethyl)methylamine*0.1H2CO3

Conditions
ConditionsYield
With sodium hydroxide In dichloromethane PhNHMe added to stirred soln. of Fe complex in CH2Cl2; B compd. added portionwise; stirred for 4 h; poured onto ice; adjusted to pH 12 (NaOH); extd. with Et2O; dried (Na2SO4); solvent evapd.; chromd. (SiO2, CHCl3-MeOH); elem. anal.;92%
1-phenyl-3-ferrocenyl-1H-pyrazole-4-carbaldehyde
918342-45-7

1-phenyl-3-ferrocenyl-1H-pyrazole-4-carbaldehyde

sodium tris(acetoxy)borohydride
56553-60-7

sodium tris(acetoxy)borohydride

(C5H5)Fe(C5H4C3H(CH2OH)N2C6H5)
918342-51-5

(C5H5)Fe(C5H4C3H(CH2OH)N2C6H5)

Conditions
ConditionsYield
With diisopropylamine In 1,2-dichloro-ethane soln. Fe complex and amine in 1,2-dichloroethane was stirred at room temp. for 1 h, NaBH(OAc)3 was added and refluxed for 30 min; react. mixt. was treated with aq. NaHCO3, extd. with CH2Cl2, washed withbrine and dried over Na2SO4, solvent was removed, residue was chromd. o n silica (CHCl3-MeOH 9:1); elem. anal.;92%
formaldehyd
50-00-0

formaldehyd

(S)-2-(tert-butoxy)-2-(6-(((cyclohexylmethyl)amino)methyl)-4-(4,4-dimethylpiperidin-1-yl)-5-(4-(4-fluorophenethoxy)phenyl)-2-methylpyridin-3-yl)acetic acid

(S)-2-(tert-butoxy)-2-(6-(((cyclohexylmethyl)amino)methyl)-4-(4,4-dimethylpiperidin-1-yl)-5-(4-(4-fluorophenethoxy)phenyl)-2-methylpyridin-3-yl)acetic acid

sodium tris(acetoxy)borohydride
56553-60-7

sodium tris(acetoxy)borohydride

(S)-2-(tert-butoxy)-2-(6-(((cyclohexylmethyl)(methyl)amino)methyl)-4-(4,4-dimethylpiperidin-1-yl)-5-(4-(4-fluorophenethoxy)phenyl)-2-methylpyridin-3-yl)acetic acid

(S)-2-(tert-butoxy)-2-(6-(((cyclohexylmethyl)(methyl)amino)methyl)-4-(4,4-dimethylpiperidin-1-yl)-5-(4-(4-fluorophenethoxy)phenyl)-2-methylpyridin-3-yl)acetic acid

Conditions
ConditionsYield
Stage #1: formaldehyd; (S)-2-(tert-butoxy)-2-(6-(((cyclohexylmethyl)amino)methyl)-4-(4,4-dimethylpiperidin-1-yl)-5-(4-(4-fluorophenethoxy)phenyl)-2-methylpyridin-3-yl)acetic acid In methanol; water at 20℃; for 2h;
Stage #2: sodium tris(acetoxy)borohydride In methanol; water for 3h;
92%
ferrocenecarboxaldehyde
12093-10-6

ferrocenecarboxaldehyde

methyl L-isoleucinate hydrochloride
18598-74-8

methyl L-isoleucinate hydrochloride

sodium tris(acetoxy)borohydride
56553-60-7

sodium tris(acetoxy)borohydride

N-(ferrocenylmethyl)-L-isoleucine methyl ester

N-(ferrocenylmethyl)-L-isoleucine methyl ester

Conditions
ConditionsYield
With sodium hydroxide; triethylamine In tetrahydrofuran isoleucine methyl ester and Et3N added to stirred soln. of Fe complex inTHF; B compd. added portionwise; stirred for 4 h; poured onto ice; adju sted to pH 12 (NaOH); extd. with Et2O; dried (Na2SO4); solvent evapd.; chromd. (SiO2, CHCl3-MeOH); elem. anal.;91.8%
(3S,4S)-tert-butyl 3-((6-(bis(tert-butoxycarbonyl)amino)-4-methylpyridin-2-yl)methyl)-4-(2-oxoethoxy)pyrrolidine-1-carboxylate
1367074-76-7

(3S,4S)-tert-butyl 3-((6-(bis(tert-butoxycarbonyl)amino)-4-methylpyridin-2-yl)methyl)-4-(2-oxoethoxy)pyrrolidine-1-carboxylate

sodium tris(acetoxy)borohydride
56553-60-7

sodium tris(acetoxy)borohydride

2-fluorobenzylamine
89-99-6

2-fluorobenzylamine

(3S,4S)-tert-butyl 3-((6-(bis(tert-butoxycarbonyl)amino)-4-methylpyridin-2-yl)methyl)-4-(2-(2-fluorobenzylamino)ethoxy)pyrrolidine-1-carboxylate
1367074-77-8

(3S,4S)-tert-butyl 3-((6-(bis(tert-butoxycarbonyl)amino)-4-methylpyridin-2-yl)methyl)-4-(2-(2-fluorobenzylamino)ethoxy)pyrrolidine-1-carboxylate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 3h;91%
sodium tris(acetoxy)borohydride
56553-60-7

sodium tris(acetoxy)borohydride

(1S,2R)-(3-amino-1-benzyl-2-hydroxy-propyl)-carbamic acid tert butyl ester
162536-42-7

(1S,2R)-(3-amino-1-benzyl-2-hydroxy-propyl)-carbamic acid tert butyl ester

tert-Butyl N-(1S,2R)-1-benzyl-3-[(4-cyano-2,2-dimethylbutyl)amino]-2-hydroxypropylcarbamate
288295-69-2

tert-Butyl N-(1S,2R)-1-benzyl-3-[(4-cyano-2,2-dimethylbutyl)amino]-2-hydroxypropylcarbamate

Conditions
ConditionsYield
In tetrahydrofuran; 1,2-dichloro-ethane; N,N-dimethyl-formamide90%
1-phenyl-3-ferrocenyl-1H-pyrazole-4-carbaldehyde
918342-45-7

1-phenyl-3-ferrocenyl-1H-pyrazole-4-carbaldehyde

sodium tris(acetoxy)borohydride
56553-60-7

sodium tris(acetoxy)borohydride

methoxycarbonylmethylamine
616-34-2

methoxycarbonylmethylamine

methyl 2-[(1-phenyl-3-ferrocenyl-1-pyrazol-4-yl)methyl-amino]acetate
1259930-83-0

methyl 2-[(1-phenyl-3-ferrocenyl-1-pyrazol-4-yl)methyl-amino]acetate

Conditions
ConditionsYield
In 1,2-dichloro-ethane soln. Fe complex and amine in 1,2-dichloroethane was stirred at room temp. for 1 h, NaBH(OAc)3 was added and refluxed for 30 min; react. mixt. was treated with aq. NaHCO3, extd. with CH2Cl2, washed withbrine and dried over Na2SO4, solvent was removed, residue was chromd. o n silica (CHCl3-MeOH 9:1); elem. anal.;90%
3-ferrocenyl-1-(2-naphthyl)pyrazole-4-carbaldehyde
1259930-40-9

3-ferrocenyl-1-(2-naphthyl)pyrazole-4-carbaldehyde

sodium tris(acetoxy)borohydride
56553-60-7

sodium tris(acetoxy)borohydride

(C5H5)Fe(C5H4C3H(CH2OH)N2C10H7)
1259930-45-4

(C5H5)Fe(C5H4C3H(CH2OH)N2C10H7)

Conditions
ConditionsYield
With diisopropylamine In 1,2-dichloro-ethane soln. Fe complex and amine in 1,2-dichloroethane was stirred at room temp. for 1 h, NaBH(OAc)3 was added and refluxed for 30 min; react. mixt. was treated with aq. NaHCO3, extd. with CH2Cl2, washed withbrine and dried over Na2SO4, solvent was removed, residue was chromd. o n silica (CHCl3-MeOH 9:1); elem. anal.;90%
m-iodobenzaldehyde
696-41-3

m-iodobenzaldehyde

sodium tris(acetoxy)borohydride
56553-60-7

sodium tris(acetoxy)borohydride

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

(3-iodo-benzyl)-dimethyl-amine
141189-59-5

(3-iodo-benzyl)-dimethyl-amine

Conditions
ConditionsYield
Stage #1: m-iodobenzaldehyde; N,N-dimethyl-formamide With acetic acid In dichloromethane at 0℃;
Stage #2: sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 0.5h;
90%
3,4-dihydro-2H-pyrano[2,3-c]pyridine-6-carbaldehyde
527681-61-4

3,4-dihydro-2H-pyrano[2,3-c]pyridine-6-carbaldehyde

sodium tris(acetoxy)borohydride
56553-60-7

sodium tris(acetoxy)borohydride

(4R/S)-3-chloro-4-({4-[(3,4-dihydro-2H-pyrano[2,3-c]pyridin-6-ylmethyl)amino]-1-piperidinyl}methyl)-4-hydroxy-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one monoacetate salt

(4R/S)-3-chloro-4-({4-[(3,4-dihydro-2H-pyrano[2,3-c]pyridin-6-ylmethyl)amino]-1-piperidinyl}methyl)-4-hydroxy-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one monoacetate salt

Conditions
ConditionsYield
Stage #1: (4R/S)-4-[(4-amino-1-piperidinyl)methyl]-3-chloro-4-hydroxy-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one; 3,4-dihydro-2H-pyrano[2,3-c]pyridine-6-carbaldehyde In methanol; chloroform at 20℃; for 2h;
Stage #2: sodium tris(acetoxy)borohydride In methanol; chloroform for 2h;
88%
sodium tris(acetoxy)borohydride
56553-60-7

sodium tris(acetoxy)borohydride

phenethylamine
64-04-0

phenethylamine

A

methyl-N-(benzyl-methyl)-formamide
877-95-2

methyl-N-(benzyl-methyl)-formamide

B

N,N-diethylphenethylamine
5300-21-0

N,N-diethylphenethylamine

Conditions
ConditionsYield
In acetonitrile at 60℃; for 15h;A 6.5%
B 86.2%
1-bromo-2-methylallylamine
913983-80-9

1-bromo-2-methylallylamine

Fe(CO)3(CH3CHCHCHCHCO(CH2)3CHO)

Fe(CO)3(CH3CHCHCHCHCO(CH2)3CHO)

sodium tris(acetoxy)borohydride
56553-60-7

sodium tris(acetoxy)borohydride

E-Fe(CO)3(CH3CHCHCHCHC5H9N(CH2C(CH3)CHBr))

E-Fe(CO)3(CH3CHCHCHCHC5H9N(CH2C(CH3)CHBr))

Conditions
ConditionsYield
In tetrahydrofuran treatment of iron compd. with amine deriv. and boron compd. in THF; NMR;86%
piperidine
110-89-4

piperidine

N-(2-naphthylsulfonyl)-N'-(2-acetamido)piperazine
867066-17-9

N-(2-naphthylsulfonyl)-N'-(2-acetamido)piperazine

sodium tris(acetoxy)borohydride
56553-60-7

sodium tris(acetoxy)borohydride

N-(2-naphthylsulfonyl)-N'-(2-thioacetamido)piperazine

N-(2-naphthylsulfonyl)-N'-(2-thioacetamido)piperazine

Conditions
ConditionsYield
With sodium hydrogencarbonate In methanol; dichloromethane85%
sodium tris(acetoxy)borohydride
56553-60-7

sodium tris(acetoxy)borohydride

pyrographite
7440-44-0

pyrographite

N-(4,5-Dimethyl-3-isoxazolyl)-2'-formyl-4'-(2-oxazolyl)[1,1'-biphenyl]-2-sulfonamide
210891-12-6

N-(4,5-Dimethyl-3-isoxazolyl)-2'-formyl-4'-(2-oxazolyl)[1,1'-biphenyl]-2-sulfonamide

N-(4,5-Dimethyl-3-isoxazolyl)-2'-[(methylamino)methyl]-4'-(2-oxazolyl)[1,1'-biphenyl]-2-sulfonamide, monohydrochloride
415697-66-4

N-(4,5-Dimethyl-3-isoxazolyl)-2'-[(methylamino)methyl]-4'-(2-oxazolyl)[1,1'-biphenyl]-2-sulfonamide, monohydrochloride

Conditions
ConditionsYield
With hydrogenchloride; methylamine In methanol; ethanol; acetic acid85%

56553-60-7Relevant articles and documents

Gribble, G. W.,Ferguson, D. C.

, (1975)

Synthesis from (+)-α-pinene of optically active macrocycles containing cyclobutane, ester, azine, or hydrazide groups

Ishmuratov,Mingaleeva,Shakhanova,Muslukhov,Yakovleva,Botsman,Tolstikov

, p. 210 - 214 (2011)

Optically active symmetric macrocyclic diesterazines and diesterdihydrazides were synthesized efficiently from the available natural monoterpene (+)-α-pinene (de 50%) using a [2+1]-reaction of 1'-[(1S,3S)-3-(2-hydroxyethyl)-2,2-dimethylcyclobutyl]ethanone and glutaric and adipic acid chlorides followed by [1+1]-condensation of the intermediate diketodiesters with hydrazine hydrate or glutaric acid dihydrazide.

Two-step stereocontrolled synthesis of densely functionalized cyclic β-aminoesters containing four stereocenters, based on a new cerium(IV) ammonium nitrate catalyzed sequential three-component reaction

Sridharan, Vellaisamy,Menendez, J. Carlos

, p. 4303 - 4306 (2008)

(Chemical Equation Presented) The cerium(IV) ammonium nitrate (CAN)-catalyzed sequential, one-pot reaction between alkylamines, β-ketoesters, and chalcones afforded cis-4,6-disubstituted 2-alkylaminocyclohexene-1-carboxylic esters with complete diastereoselectivity. The carbon-carbon double bond of these compounds was reduced with sodium triacetoxyborohydride, again with complete diastereoselectivity. This novel two-step route allows the transformation of very simple acyclic starting materials into tetrasubstituted cyclohexane derivatives bearing four functional groups, including a cis-β-aminoester moiety, and generates four stereocenters, three of which are adjacent and one of which is quaternary.

Total Synthesis of Ritterazine B

Nakayama, Yasuaki,Maser, Michael R.,Okita, Tatsuya,Dubrovskiy, Anton V.,Campbell, Taryn L.,Reisman, Sarah E.

supporting information, p. 4187 - 4192 (2021/04/06)

The first total synthesis of the cytotoxic alkaloid ritterazine B is reported. The synthesis features a unified approach to both steroid subunits, employing a titanium-mediated propargylation reaction to achieve divergence from a common precursor. Other key steps include gold-catalyzed cycloisomerizations that install both spiroketals and late stage C-H oxidation to incorporate the C7′ alcohol.

Low-cost method preparation for doxazosin mesylate controlled release tablets

-

Paragraph 0017; 0018, (2019/07/01)

The invention relates to a preparation method of doxazosin mesylate controlled release tablets for treating urination disorder caused by prostatic hyperplasia, and belongs to the field of medicines. The invention provides a low-cost preparation method for doxazosin mesylate controlled release tablets.

Post a RFQ

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

1

What can I do for you?
Get Best Price

Get Best Price for 56553-60-7