TRANS-4-AMINO-1-BOC-PYRROLIDINE-3-CARBOXYLIC ACID

Base Information

• Chemical Name: TRANS-4-AMINO-1-BOC-PYRROLIDINE-3-CARBOXYLIC ACID
• CAS No.: 369623-85-8
• Molecular Formula: C10H18N2O4
• Molecular Weight: 230.26100
• Mol file: 369623-85-8.mol

Synonyms:1,3-Pyrrolidinedicarboxylic acid, 4-amino-, 1-(1,1-dimethylethyl) ester, (3R,4S)-rel-;

Chemical Property of TRANS-4-AMINO-1-BOC-PYRROLIDINE-3-CARBOXYLIC ACID

Chemical Property:

• Vapor Pressure: 1.59E-06mmHg at 25°C
• Boiling Point: 371.1ºC at 760 mmHg
• PKA: 3.53±0.20(Predicted)
• Flash Point: 178.2ºC
• PSA: 92.86000
• Density: 1.232g/cm3
• LogP: 0.90340
• Storage Temp.: 2-8°C(protect from light)

Purity/Quality:

99%, ^*data from raw suppliers

(3S,4R)-4-Amino-1-(tert-butoxycarbonyl)pyrrolidine-3-carboxylic acid 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of TRANS-4-AMINO-1-BOC-PYRROLIDINE-3-CARBOXYLIC ACID

There total 17 articles about TRANS-4-AMINO-1-BOC-PYRROLIDINE-3-CARBOXYLIC ACID which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

N-(tert-butoxycarbonyl)glycine methyl ester (31954-27-5) → (3R,4R)-4-Amino-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester (369623-85-8,492461-79-7,492462-02-9)

Guidance literature:

Multi-step reaction with 7 steps

1: sodium hydride / tetrahydrofuran / 0 °C

2: diisobutylaluminum hydride / CH₂Cl₂ / -78 °C

3: potassium carbonate / toluene / 20 °C

4: H₂ / Pd(OH)/C / 760 Torr

5: triethylamine / tetrahydrofuran / 0 °C

6: Jones reagent / acetone / 0 °C

7: H₂ / Pd/C / ethanol / 760 Torr

With jones reagent; hydrogen; sodium hydride; diisobutylaluminium hydride; potassium carbonate; triethylamine; palladium on activated charcoal; palladium hydroxide - carbon; In tetrahydrofuran; ethanol; dichloromethane; acetone; toluene;

DOI:10.1128/AAC.45.9.2563-2570.2001

Reference yield:

(3S,4R)-1-(N-tert-butoxycarbonyl)-3-[(1'R)-phenylethylamino]pyrrolidine-4-carboxylic acid ethyl ester hydrochloride (346610-81-9,267230-41-1) → (3R,4S)-4-Amino-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester (369623-85-8,492461-79-7,492462-02-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: Pd/C; H₂ / ethanol / 22 h / 20 °C / 2585.81 Torr

1.2: 90 percent / NaHCO₃ / acetone; H₂O / 14 h / 20 °C

2.1: LiOH / methanol; H₂O / 15 h / 0 °C

3.1: H₂ / Pd/C

With lithium hydroxide; palladium on activated charcoal; hydrogen; palladium on activated charcoal; In methanol; ethanol; water; 1.1: Hydrogenolysis / 1.2: Acylation / 2.1: Hydrolysis / 3.1: Hydrogenolysis;

DOI:10.1021/ja000093k

Reference yield:

(3R,4S)-4-Benzyloxycarbonylamino-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester (267230-42-2) → (3R,4S)-4-Amino-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester (369623-85-8,492461-79-7,492462-02-9)

Guidance literature:

Multi-step reaction with 2 steps

1: LiOH / methanol; H₂O / 15 h / 0 °C

2: H₂ / Pd/C

With lithium hydroxide; hydrogen; palladium on activated charcoal; In methanol; water; 1: Hydrolysis / 2: Hydrogenolysis;

DOI:10.1021/ja000093k

upstream raw materials:

(3R,4S)-4-Benzyloxycarbonylamino-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester

(3R,4S)-4-Benzyloxycarbonylamino-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester

(3S,4R)-1-(N-tert-butoxycarbonyl)-3-[(1'R)-phenylethylamino]pyrrolidine-4-carboxylic acid ethyl ester hydrochloride

(3R,4S)-4-[(R)-1-phenyl-ethylamino]-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester

Downstream raw materials:

(3R,4S)-1-(N-tert-butoxycarbonyl)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-4-hydroxycarbonylpyrrolidine

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