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13726-69-7

Basic Information
CAS No.: 13726-69-7
Name: Boc-L-Hydroxyproline
Molecular Structure:
Molecular Structure of 13726-69-7 (Boc-L-Hydroxyproline)
Formula: C10H17NO5
Molecular Weight: 231.25
Synonyms: Boc-trans-4-hydroxy-L-proline;4-Hydroxy-Pyrrolidine-1,2-Dicarboxylic Acid 1-tert-Butyl Ester;Boc-L-4-hydroxyproline;N-Boc-L-hydroxyproline;(2S,4R)-N-alpha-t-butoxycarbonyl-4-hydroxypyrrolidine-2-car boxylic acid;Boc-4-hydroxy-L-proline;Boc-L-Hyp-OH;Boc-(2S,4R)-hydroxyproline;
EINECS: 604-011-7
Density: 1.312 g/cm3
Melting Point: 123-127 °C(lit.)
Boiling Point: 390.9 °C at 760 mmHg
Flash Point: 190.2 °C
Solubility: very faint turbidity
Appearance:
Hazard Symbols:
Risk Codes:
Safety: 22-24/25
Transport Information:
PSA: 87.07000
LogP: 0.37920
Synthetic route
24424-99-5

di-tert-butyl dicarbonate

51-35-4

4R-4-hydroxyproline

13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
With sodium hydroxide In water; acetone at 50℃; for 1h;100%
In tetrahydrofuran; water at 20℃; for 12h;100%
With sodium hydroxide In tetrahydrofuran; water at 20℃;100%
4N-sodium hydroxide

4N-sodium hydroxide

24424-99-5

di-tert-butyl dicarbonate

51-35-4, 913000-57-4

4-hydroxyproline

13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
With hydrogenchloride In methanol; ethyl acetate96%
74844-91-0

1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate

13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
With water; lithium hydroxide In methanol at 20℃; for 1h;58%
With sodium hydroxide In tetrahydrofuran at 0℃; for 19h;
Stage #1: 1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate With water; sodium hydroxide In methanol for 4h;
Stage #2: With citric acid In methanol; water pH=3; Product distribution / selectivity;
Stage #1: 1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate With methanol; water; lithium hydroxide at 20℃; Inert atmosphere;
Stage #2: With hydrogenchloride In water; acetonitrile for 0.166667h; Cooling with ice bath; Inert atmosphere;
34619-03-9

tert-butyldicarbonate

51-35-4

4R-4-hydroxyproline

13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
With sodium hydrogencarbonate In 1,4-dioxane; water at 20℃;97%
With sodium hydroxide In water; tert-butyl alcohol at 20℃; for 16h;89%
With sodium hydrogencarbonate In water
51-35-4

4R-4-hydroxyproline

13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
In water95%
184046-78-4

(2S,3S)-1-tert-butyl-2-methyl 3-hydroxypyrrolidine-1,2-dicarboxylate

13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Stage #1: (2S,3S)-1-tert-butyl-2-methyl 3-hydroxypyrrolidine-1,2-dicarboxylate With water; sodium hydroxide In methanol for 6h;
Stage #2: With citric acid In methanol; water pH=3;

potassium hydrogen sulphate

24424-99-5

di-tert-butyl dicarbonate

51-35-4, 913000-57-4

4-hydroxyproline

13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
In sodium hydroxide; hexane; water; tert-butyl alcohol
In sodium hydroxide; hexane; water; tert-butyl alcohol
In sodium hydroxide; hexane; water; tert-butyl alcohol
In sodium hydroxide; hexane; water; tert-butyl alcohol
51-35-4, 913000-57-4

4-hydroxyproline

13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
With sodium hydroxide In 1,4-dioxane
3236-56-4

dipercarbonate de O,O-t-butyle

51-35-4

4R-4-hydroxyproline

13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide; ammonium chloride In tetrahydrofuran; water
115352-39-1, 124662-61-9, 110339-26-9

(2R)-1-benzyloxy-2-hydroxy-pent-4-yne

13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: hydrogen / Pd/CaCO3 / ethyl acetate
2: di-isopropyl azodicarboxylate, Ph3P / tetrahydrofuran / 12 h / -20 °C
3: hydrazine / ethanol / 6 h / Heating
4: Et3N / CH2Cl2
5: 78 percent / I2 / tetrahydrofuran; H2O / 6 h / 20 °C
6: Et3N / CH2Cl2
7: RuCl3*H2O, NaIO4, / CCl4; acetonitrile; H2O / 1 h / Ambient temperature
8: K2CO3 / methanol
View Scheme
84348-37-8

N-tert-butoxycarbonyl-4-oxo-L-proline

13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 90 percent / sodium borohydride / methanol / 3.5 h / 0 °C
2: 62 percent / aq. NaOH / diethyl ether / 24 h
3: 36 percent / lithium triethylborodeuteride / tetrahydrofuran / 24 h / Heating
4: trifluoroacetic acid / 0.5 h
5: TES buffer, iron(II)ammonium sulphate, 2-oxoglutarate, proline 4-hydroxylase / 4 h / 26 °C / incubation
6: 85 percent / aq. NaOH / 2-methyl-propan-2-ol / 18 h
View Scheme
87691-27-8

N-tert-butoxycarbonyl-L-cis-4-hydroxyproline

13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 62 percent / aq. NaOH / diethyl ether / 24 h
2: 36 percent / lithium triethylborodeuteride / tetrahydrofuran / 24 h / Heating
3: trifluoroacetic acid / 0.5 h
4: TES buffer, iron(II)ammonium sulphate, 2-oxoglutarate, proline 4-hydroxylase / 4 h / 26 °C / incubation
5: 85 percent / aq. NaOH / 2-methyl-propan-2-ol / 18 h
View Scheme
153790-69-3

(2S,4R)-<4-2H1>-proline

13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: TES buffer, iron(II)ammonium sulphate, 2-oxoglutarate, proline 4-hydroxylase / 4 h / 26 °C / incubation
2: 85 percent / aq. NaOH / 2-methyl-propan-2-ol / 18 h
View Scheme

C10H16(2)HNO4

13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: trifluoroacetic acid / 0.5 h
2: TES buffer, iron(II)ammonium sulphate, 2-oxoglutarate, proline 4-hydroxylase / 4 h / 26 °C / incubation
3: 85 percent / aq. NaOH / 2-methyl-propan-2-ol / 18 h
View Scheme
153790-67-1

N-Boc-D-cis-4-(p-toluenesulfonyloxy)proline

13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 36 percent / lithium triethylborodeuteride / tetrahydrofuran / 24 h / Heating
2: trifluoroacetic acid / 0.5 h
3: TES buffer, iron(II)ammonium sulphate, 2-oxoglutarate, proline 4-hydroxylase / 4 h / 26 °C / incubation
4: 85 percent / aq. NaOH / 2-methyl-propan-2-ol / 18 h
View Scheme
90600-20-7

(2S)-2-[(tert-butoxycarbonyl)amino]pent-4-enoic acid

13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 73 percent / N-bromosuccinimide / tetrahydrofuran / 0.33 h / 0 °C
2: 100 percent / K2CO3 / 0.5 h / 0 °C
3: 1) 0.5 N NaOH, 2) dl-10-camphorsulfonic acid / 1) THF, 0 deg C, 14 h, 2) CH2Cl2, RT, 20 h
4: 1) (COCl)2, DMSO, 2) NEt3 / 1a) CH2Cl2, -78 deg C, 15 min, 1b) -45 deg C, 1 h, 2a) -45 deg C, 20 min, 2b) 0 deg C, 15 min
5: 78 percent / p-TsOH*H2O / 14 h / Ambient temperature
6: 1) 60percent HOAc, 2) NaBH3CN, HOAc / 1) RT, 3 d, 2) EtOH, RT, 1 h
7: 0.5 N NaOH / tetrahydrofuran / 19 h / 0 °C
View Scheme
104241-30-7

(2S,4S)-2-(tert-butoxycarbonyl)amino-4-bromomethyl-γ-butyrolactone

13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 100 percent / K2CO3 / 0.5 h / 0 °C
2: 1) 0.5 N NaOH, 2) dl-10-camphorsulfonic acid / 1) THF, 0 deg C, 14 h, 2) CH2Cl2, RT, 20 h
3: 1) (COCl)2, DMSO, 2) NEt3 / 1a) CH2Cl2, -78 deg C, 15 min, 1b) -45 deg C, 1 h, 2a) -45 deg C, 20 min, 2b) 0 deg C, 15 min
4: 78 percent / p-TsOH*H2O / 14 h / Ambient temperature
5: 1) 60percent HOAc, 2) NaBH3CN, HOAc / 1) RT, 3 d, 2) EtOH, RT, 1 h
6: 0.5 N NaOH / tetrahydrofuran / 19 h / 0 °C
View Scheme
104241-32-9

(2S,4R)-2-tert-butoxycarbonylamino-4-hydroxymethyl-4-butanolide

13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 1) (COCl)2, DMSO, 2) NEt3 / 1a) CH2Cl2, -78 deg C, 15 min, 1b) -45 deg C, 1 h, 2a) -45 deg C, 20 min, 2b) 0 deg C, 15 min
2: 78 percent / p-TsOH*H2O / 14 h / Ambient temperature
3: 1) 60percent HOAc, 2) NaBH3CN, HOAc / 1) RT, 3 d, 2) EtOH, RT, 1 h
4: 0.5 N NaOH / tetrahydrofuran / 19 h / 0 °C
View Scheme
106391-74-6

(2S,4R)-2-(tert-butoxycarbonyl)amino-4-formyl-γ-butyrolactone

13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 78 percent / p-TsOH*H2O / 14 h / Ambient temperature
2: 1) 60percent HOAc, 2) NaBH3CN, HOAc / 1) RT, 3 d, 2) EtOH, RT, 1 h
3: 0.5 N NaOH / tetrahydrofuran / 19 h / 0 °C
View Scheme
104241-31-8

(2S,4S)-2-(tert-butoxycarbonyl)amino-3,4-epoxypentanoic acid methyl ester

13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 1) 0.5 N NaOH, 2) dl-10-camphorsulfonic acid / 1) THF, 0 deg C, 14 h, 2) CH2Cl2, RT, 20 h
2: 1) (COCl)2, DMSO, 2) NEt3 / 1a) CH2Cl2, -78 deg C, 15 min, 1b) -45 deg C, 1 h, 2a) -45 deg C, 20 min, 2b) 0 deg C, 15 min
3: 78 percent / p-TsOH*H2O / 14 h / Ambient temperature
4: 1) 60percent HOAc, 2) NaBH3CN, HOAc / 1) RT, 3 d, 2) EtOH, RT, 1 h
5: 0.5 N NaOH / tetrahydrofuran / 19 h / 0 °C
View Scheme

(4R)-N-(tert-butoxycarbonyl)-4-hydroxy-5-methoxyproline methyl ester

13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1) 60percent HOAc, 2) NaBH3CN, HOAc / 1) RT, 3 d, 2) EtOH, RT, 1 h
2: 0.5 N NaOH / tetrahydrofuran / 19 h / 0 °C
View Scheme
121795-00-4

(2S,4R)-4-(benzyloxy)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid

13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
With potassium carbonate In methanol
58931-16-1, 88981-35-5, 110339-28-1

(R)-1-benzyloxypent-4-en-2-ol

13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: di-isopropyl azodicarboxylate, Ph3P / tetrahydrofuran / 12 h / -20 °C
2: hydrazine / ethanol / 6 h / Heating
3: Et3N / CH2Cl2
4: 78 percent / I2 / tetrahydrofuran; H2O / 6 h / 20 °C
5: Et3N / CH2Cl2
6: RuCl3*H2O, NaIO4, / CCl4; acetonitrile; H2O / 1 h / Ambient temperature
7: K2CO3 / methanol
View Scheme
121794-95-4

(S)-1-(benzyloxy)pent-4-en-2-amine

13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: Et3N / CH2Cl2
2: 78 percent / I2 / tetrahydrofuran; H2O / 6 h / 20 °C
3: Et3N / CH2Cl2
4: RuCl3*H2O, NaIO4, / CCl4; acetonitrile; H2O / 1 h / Ambient temperature
5: K2CO3 / methanol
View Scheme
121794-96-5

N-((S)-1-Benzyloxymethyl-but-3-enyl)-benzamide

13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 78 percent / I2 / tetrahydrofuran; H2O / 6 h / 20 °C
2: Et3N / CH2Cl2
3: RuCl3*H2O, NaIO4, / CCl4; acetonitrile; H2O / 1 h / Ambient temperature
4: K2CO3 / methanol
View Scheme
121794-97-6

O-benzyl-(2S,4R)-4-benzoyloxyprolinol

13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: Et3N / CH2Cl2
2: RuCl3*H2O, NaIO4, / CCl4; acetonitrile; H2O / 1 h / Ambient temperature
3: K2CO3 / methanol
View Scheme
121794-94-3

2-((S)-1-Benzyloxymethyl-but-3-enyl)-isoindole-1,3-dione

13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: hydrazine / ethanol / 6 h / Heating
2: Et3N / CH2Cl2
3: 78 percent / I2 / tetrahydrofuran; H2O / 6 h / 20 °C
4: Et3N / CH2Cl2
5: RuCl3*H2O, NaIO4, / CCl4; acetonitrile; H2O / 1 h / Ambient temperature
6: K2CO3 / methanol
View Scheme
121794-98-7

(2S,4R)-4-Benzoyloxy-2-benzyloxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: RuCl3*H2O, NaIO4, / CCl4; acetonitrile; H2O / 1 h / Ambient temperature
2: K2CO3 / methanol
View Scheme
51-35-4

4R-4-hydroxyproline

BocON

BocON

13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
With triethylamine
1070-19-5

N-(tert-butyloxycarbonyl) azide

51-35-4

4R-4-hydroxyproline

13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

74844-91-0

1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate

Conditions
ConditionsYield
In methanol100%
In methanol; diethyl ether100%
In tetrahydrofuran96%
100-39-0

benzyl bromide

13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

40350-83-2, 54631-82-2, 54631-81-1

(2S,4R)-4-(benzyloxy)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Stage #1: (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid With sodium hydride In tetrahydrofuran; dimethyl sulfoxide; mineral oil at -20 - 0℃; Inert atmosphere;
Stage #2: benzyl bromide In tetrahydrofuran; dimethyl sulfoxide; mineral oil at -20 - 25℃; for 6h; Inert atmosphere; chemoselective reaction;
100%
Stage #1: (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 1h; Inert atmosphere;
Stage #2: benzyl bromide In tetrahydrofuran; mineral oil Inert atmosphere;
90%
With sodium hydride; 18-crown-6 ether 1.) THF, 0 degC, 1 h, and 30 min, RT, 2.) 0 degC, 1 h and 50 degC, overnight, THF; Yield given. Multistep reaction;
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

126090-32-2

N-methyl-N-(phenylmethyl)-L-phenylalaninamide hydrochloride

131949-55-8

Boc-(2S,4R)Hyp-Phe-NMeBzl

Conditions
ConditionsYield
With benzotriazol-1-ol In dichloromethane Ambient temperature;100%
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

109384-24-9

tert-butyl (2S,4R)-2-(aminocarbonyl)-4-hydroxypyrrolidine-1-carboxylate

Conditions
ConditionsYield
Stage #1: (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid With 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In acetonitrile at 20℃; for 6h;
Stage #2: With ammonium hydroxide In acetonitrile at 0 - 20℃; for 1.5h;
100%
Stage #1: (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid With chloroformic acid ethyl ester; triethylamine In tetrahydrofuran at -15℃; for 0.166667h; Inert atmosphere;
Stage #2: With ammonia In tetrahydrofuran; water at -15 - 5℃; for 2h;
86%
Stage #1: (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid With chloroformic acid ethyl ester; triethylamine In tetrahydrofuran at -10℃; for 1h;
Stage #2: With ammonia In tetrahydrofuran; water at -5 - 20℃; for 2h;
59%
Stage #1: (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid With 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In acetonitrile at 20℃;
Stage #2: With ammonium hydroxide In acetonitrile
Stage #1: (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane; N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: With ammonium chloride In dichloromethane; N,N-dimethyl-formamide at 20℃; for 2h;
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

18107-18-1

diazomethyl-trimethyl-silane

74844-91-0

1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate

Conditions
ConditionsYield
In methanol at 0℃; for 1h;100%
In methanol; hexane; benzene at 20℃; for 1h;
In tetrahydrofuran; methanol; toluene at -78 - 23℃; for 0.166667h; Inert atmosphere;
884538-46-9

7-chloro-5-pyridin-2-ylthieno[3,2-b]pyridine

13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

884538-47-0

(2S,4R)-1-(tert-butoxycarbonyl)-4-(5-(pyridin-2-yl)thieno[3,2-b]pyridin-7-yloxy)pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
With potassium tert-butylate In dimethyl sulfoxide at 20℃; for 70h;100%
Stage #1: (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid With potassium tert-butylate In dimethyl sulfoxide for 2h;
Stage #2: 7-chloro-5-pyridin-2-ylthieno[3,2-b]pyridine In dimethyl sulfoxide at 30℃; for 90h;
Stage #3: With hydrogenchloride In water pH=4.5;
57%
132997-77-4

1-chloro-6-methoxyisoquinoline

13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

630421-67-9

(2S,4R)-1-(tert-butoxycarbonyl)-4-((6-methoxyisoquinolin-1-yl)oxy)pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Stage #1: (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid With potassium tert-butylate In dimethyl sulfoxide at 20℃; for 2h;
Stage #2: 1-chloro-6-methoxyisoquinoline In dimethyl sulfoxide at 20℃; for 12h;
100%
Stage #1: (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid With potassium tert-butylate In dimethyl sulfoxide at 20℃; for 0.5h;
Stage #2: 1-chloro-6-methoxyisoquinoline In dimethyl sulfoxide at 20℃; for 12h;
99%
Stage #1: (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid With potassium tert-butylate In dimethyl sulfoxide at 10 - 20℃; for 0.5h;
Stage #2: 1-chloro-6-methoxyisoquinoline In dimethyl sulfoxide at 20℃; for 12h;
99%
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

106-95-6

allyl bromide

93962-39-1

(2S,4R)-4-(but-3-en-1-yloxy)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Stage #1: (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid With sodium hydride In tetrahydrofuran; dimethyl sulfoxide; mineral oil at -20 - 0℃; Inert atmosphere;
Stage #2: allyl bromide In tetrahydrofuran; dimethyl sulfoxide; mineral oil at -20 - 25℃; for 6h; Inert atmosphere; chemoselective reaction;
100%
Stage #1: (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid; allyl bromide With sodium hydride In N,N-dimethyl-formamide at -25 - 20℃;
Stage #2: With sodium hydroxide In methanol at 0 - 20℃;
67%
Stage #1: (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid With sodium hydroxide In tetrahydrofuran; mineral oil at 20℃; for 1h; Inert atmosphere;
Stage #2: allyl bromide With 18-crown-6 ether In tetrahydrofuran; mineral oil at 20 - 50℃;
7742-73-6

1,3-dichloroisoquinoline

13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

630425-54-6

C19H21ClN2O5

Conditions
ConditionsYield
Stage #1: (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid With sodium hydride In DMF (N,N-dimethyl-formamide) at 0℃; for 0.5h;
Stage #2: 1,3-dichloroisoquinoline In DMF (N,N-dimethyl-formamide) at 20℃; for 12h;
99.8%
1448189-30-7

1-[4-(4-methyl-1,3-thiazol-5-yl)phenyl]methaneamine

13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

1448191-54-5

tert‐butyl (2S,4R)‐4‐hydroxy‐2‐({[4‐(4‐methyl‐1,3‐thiazol‐5‐yl)phenyl]methyl}carbamoyl)pyrrolidine‐1‐carboxylate

Conditions
ConditionsYield
Stage #1: (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid With triethylamine In N,N-dimethyl-formamide at 0℃; for 0.0833333h;
Stage #2: 1-[4-(4-methyl-1,3-thiazol-5-yl)phenyl]methaneamine In N,N-dimethyl-formamide at 20℃;
99.49%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide for 15h;98%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide for 15h;98%
853269-47-3

1-ethyl-cyclopropane-sulfonic acid [1(R)-amino-2(S)-vinyl-cyclopropanecarbonyl]-amide hydrochloride

13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

853269-48-4

2(S)-[1(R)-(1-ethyl-cyclopropanesulfonylaminocarbonyl)-2(S)-vinyl-cyclopropylcarbamoyl]-4(R)-hydroxy-N-Boc-pyrrolidone

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate In dichloromethane at 20℃; for 1h;99%
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

1794-48-5

1-bromo-3-phenylprop-2-yne

872496-90-7

C19H23NO5

Conditions
ConditionsYield
Stage #1: (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid With sodium hydride at 20℃; for 1h;
Stage #2: 1-bromo-3-phenylprop-2-yne for 16h; Heating / reflux;
99%
67-56-1

methanol

13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

40216-83-9

L-4-hydroxyproline methyl ester hydrochloride

Conditions
ConditionsYield
With hydrogenchloride at 20℃; for 12h;99%
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

589-15-1

1-bromomethyl-4-bromobenzene

1374041-49-2

C17H22BrNO5

Conditions
ConditionsYield
With caesium carbonate In 1-methyl-pyrrolidin-2-one at 0 - 20℃;99%
With caesium carbonate In 1-methyl-pyrrolidin-2-one at 0 - 20℃;99%
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

103-67-3

benzyl-methyl-amine

330583-66-9

(2S,4R)-2-(Benzyl-methyl-carbamoyl)-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 6h;98%
189816-05-5

4-chloro-7-methoxy-2-phenylquinoline

13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

259214-37-4

(2S,4R)-1-(tert-butoxycarbonyl)-4-(7-methoxy-2-phenylquinolin-4-yloxy)pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Stage #1: (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid With potassium tert-butylate In dimethyl sulfoxide at 0℃; for 1.5h;
Stage #2: 4-chloro-7-methoxy-2-phenylquinoline In dimethyl sulfoxide for 25h;
98%
Stage #1: (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid With potassium tert-butylate In dimethyl sulfoxide at 0℃; for 1.5h;
Stage #2: 4-chloro-7-methoxy-2-phenylquinoline In dimethyl sulfoxide for 25h;
98%
Stage #1: (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid With potassium tert-butylate In dimethyl sulfoxide at 0℃; for 1.5h;
Stage #2: 4-chloro-7-methoxy-2-phenylquinoline In dimethyl sulfoxide for 24h;
Stage #3: pH=4.6; Acidic aqueous solution;
98%
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

18162-48-6

tert-butyldimethylsilyl chloride

74-88-4

methyl iodide

1374161-77-9

(2S,4R)-4-(tert-butyldimethylsilanyloxy)-2-methylpyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester

Conditions
ConditionsYield
Stage #1: (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid; methyl iodide With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃; for 5h;
Stage #2: tert-butyldimethylsilyl chloride With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃; for 2h;
98%
1448189-30-7

1-[4-(4-methyl-1,3-thiazol-5-yl)phenyl]methaneamine

13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

(2S,4R)-tert-butyl 4-hydroxy-2-((4-(4-methylthiazol-5-yl)benzyl)carbamoyl)pyrrolidine-1-carboxylate

Conditions
ConditionsYield
Stage #1: (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide for 0.0833333h;
Stage #2: [4-(4-methyl-1,3-thiazol-5-yl)phenyl]methanamine In N,N-dimethyl-formamide for 15h;
98%
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

87250-97-3, 113775-22-7

2’-methyl-2’-propanyl (1S,4S)-3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 20h; Mitsunobu reaction;97%
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; for 20h; Mitsunobu Displacement; Inert atmosphere;87%
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran82%
746657-36-3

(1R,2S)-ethyl 1-amino-2-vinylcyclopropanecarboxylate

13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

862119-82-2

(2S,4R)-tert-butyl 2-((1R,2S)-1-(ethoxycarbonyl)-2-vinylcyclopropylcarbamoyl)-4-hydroxypyrrolidine-1-carboxylate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 0 - 20℃;97%
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 0 - 20℃;96%
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 0 - 20℃;96%
1159609-95-6

(1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid ethyl ester tosylate salt

13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

862119-82-2

(2S,4R)-tert-butyl 2-((1R,2S)-1-(ethoxycarbonyl)-2-vinylcyclopropylcarbamoyl)-4-hydroxypyrrolidine-1-carboxylate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 0 - 20℃; for 4.5h;97%
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 0 - 20℃;89%
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

58479-61-1

tert-butylchlorodiphenylsilane

1357471-22-7

trans-4-tert-butyldiphenylsiloxy-N-Boc-L-proline carboxylic acid

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 50℃; for 4h; Reflux;97%
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

61478-26-0

tert-butyl (2S,4R)-4-hydroxy-2-hydroxymethyl-pyrrolidine-1-carboxylate

Conditions
ConditionsYield
Stage #1: (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid With borane-THF In tetrahydrofuran at 0 - 20℃; for 4.25h;
Stage #2: With methanol In tetrahydrofuran at 20℃; for 62h;
96%
Stage #1: (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid With borane-THF In tetrahydrofuran at 0 - 20℃; for 4.25h;
Stage #2: With methanol In tetrahydrofuran at 0 - 20℃; for 62h;
96%
With borane-THF at 0℃; for 1h; Inert atmosphere;96%
19493-44-8

1-chloroisoquinoline

13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

630421-77-1

4-(isoquinoline-1-yloxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester

Conditions
ConditionsYield
Stage #1: 1-chloroisoquinoline; (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid With potassium tert-butylate In dimethyl sulfoxide at 0 - 20℃; for 25.7167h;
Stage #2:
Stage #3: With hydrogenchloride In water
96%
Stage #1: (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid With potassium tert-butylate In dimethyl sulfoxide at 10 - 20℃; for 0.5h;
Stage #2: 1-chloroisoquinoline In dimethyl sulfoxide at 20℃; for 12h;
Stage #3: With citric acid In water; dimethyl sulfoxide at 0℃; Product distribution / selectivity;
92%

ethyl (1R,2S)-1-amino-2-vinylcyclopropanecarboxylate hydrochloride

13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

862119-82-2

(2S,4R)-tert-butyl 2-((1R,2S)-1-(ethoxycarbonyl)-2-vinylcyclopropylcarbamoyl)-4-hydroxypyrrolidine-1-carboxylate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 0 - 20℃; Product distribution / selectivity;96%
With 4-methyl-morpholine; HATU In dichloromethane at 20℃; for 18h;94%
With 4-methyl-morpholine; HATU In dichloromethane at 20℃; for 18h;94%
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

107-08-4

1-iodo-propane

146129-07-9

(2S,4R)-1-(tert-butoxycarbonyl)-4-propoxypyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Stage #1: (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid With sodium hydride In tetrahydrofuran; dimethyl sulfoxide; mineral oil at -20 - 0℃; Inert atmosphere;
Stage #2: 1-iodo-propane In tetrahydrofuran; dimethyl sulfoxide; mineral oil at -20 - 25℃; for 24h; Inert atmosphere; chemoselective reaction;
96%
13368-25-7

1-(bromomethyl)-4-vinylbenzene

13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

(2S,4R)-1-(tert-butoxycarbonyl)-4-((4-vinylbenzyl)oxy)pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Stage #1: (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid With sodium hydride In tetrahydrofuran; dimethyl sulfoxide; mineral oil at -20 - 0℃; Inert atmosphere;
Stage #2: 1-(bromomethyl)-4-vinylbenzene In tetrahydrofuran; dimethyl sulfoxide; mineral oil at -20 - 25℃; for 24h; Inert atmosphere; chemoselective reaction;
96%
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    Boc-L-Hydroxyproline

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    trans-N-(tert-Butoxycarbonyl)-4-hydroxy-L-proline

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    Product Name: Boc-L-Hydroxyproline CAS: 13726-69-7 MF: C10H17NO5 MW: 231.25 EINECS: 604-011-7 Mol File: 13726-69-7.mol Boc-L-Hydroxyproline Structure Boc-L-Hydroxyproline Chemical Properties Melting point 123-127 °C(lit.)

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Chemistry

Molecular structure of Boc-L-Hydroxyproline (CAS NO.13726-69-7) is:

Product Name: Boc-L-Hydroxyproline
CAS Registry Number: 13726-69-7
IUPAC Name: (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
Molecular Weight: 231.24568 [g/mol]
Molecular Formula: C10H17NO5
XLogP3-AA: 0.3
H-Bond Donor: 2
H-Bond Acceptor: 5
Melting Point: 123-127 °C(lit.)
Surface Tension: 57 dyne/cm
Density: 1.312 g/cm3
Flash Point: 190.2 °C
Enthalpy of Vaporization: 74.05 kJ/mol
Boiling Point: 390.9 °C at 760 mmHg
Vapour Pressure: 9.99E-08 mmHg at 25°C
Product Categories: Aminoacids derivatives;Pyrrole&Pyrrolidine&Pyrroline;Amino Acids;Hydroxyproline [Hyp];Unusual Amino Acids;Amino Acids (N-Protected);Biochemistry;Boc-Amino Acids;Boc-Amino acid series

Safety Profile

Safety Statements: 22-24/25 
S22:Do not breathe dust. 
S24/25:Avoid contact with skin and eyes.
WGK Germany: 3
HazardClass: IRRITANT

Specification

 Boc-L-Hydroxyproline , its cas register number is 13726-69-7. It also can be called trans-N-(tert-Butoxycarbonyl)-4-hydroxy-L-proline ; Boc-Hyp-OH ; (2S,4R)-1-tert-Butyl 4-hydroxy-1,2-pyrrolidinecarboxylate ; 1,2-Pyrrolidinedicarboxylic acid, 4-hydroxy-, 1-(1,1-dimethylethyl) ester, (2S,4R)- .