(R)-1-(Tert-butoxycarbonyl)-4,4-difluoropyrrolidine-2-carboxylic acid

Base Information

• Chemical Name: (R)-1-(Tert-butoxycarbonyl)-4,4-difluoropyrrolidine-2-carboxylic acid
• CAS No.: 536747-87-2
• Molecular Formula: C10H15F2NO4
• Molecular Weight: 251.22700
• European Community (EC) Number: 867-453-1
• Mol file: 536747-87-2.mol

Synonyms:536747-87-2;(R)-1-(TERT-BUTOXYCARBONYL)-4,4-DIFLUOROPYRROLIDINE-2-CARBOXYLIC ACID;(R)-1-Boc-4,4-difluoropyrrolidine-2-carboxylic acid;(2R)-1-[(tert-butoxy)carbonyl]-4,4-difluoropyrrolidine-2-carboxylic acid;(2R)-4,4-difluoro-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic Acid;C10H15F2NO4;MFCD08272893;(2r)-1-((tert-butoxy)carbonyl)-4,4-difluoropyrrolidine-2-carboxylic acid;SCHEMBL1848946;AMY7155;WTMZYKCXBXPVPT-ZCFIWIBFSA-M;WTMZYKCXBXPVPT-ZCFIWIBFSA-N;BOC-D-PRO(4,4-DIFLUORO);AKOS025290362;PB36828;AS-42540;CS-0053507;EN300-364371;W-206509;(2R)-1-Boc-4,4-Difluoropyrrolidine-2-Carboxylic Acid;(R)-1-(TERT-BUTOXYCARBONYL)-4,4-DIFLUOROPYRROLIDINE-2-CARBOXYLICACID;1,2-Pyrrolidinedicarboxylic acid, 4,4-difluoro-, 1-(1,1-dimethylethyl)ester, (2R)-

Chemical Property of (R)-1-(Tert-butoxycarbonyl)-4,4-difluoropyrrolidine-2-carboxylic acid

Chemical Property:

• Boiling Point: 340.4±42.0 °C(Predicted)
• PKA: 3.06±0.40(Predicted)
• PSA: 66.84000
• Density: 1.31±0.1 g/cm3(Predicted)
• LogP: 1.65360
• Storage Temp.: 2-8°C
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 251.09691428
• Heavy Atom Count: 17
• Complexity: 338

Purity/Quality:

98%,99%, ^*data from raw suppliers

(2R)-1-[(tert-Butoxy)carbonyl]-4,4-difluoropyrrolidine-2-carboxylic acid 97.0% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CC(CC1C(=O)O)(F)F
• Isomeric SMILES: CC(C)(C)OC(=O)N1CC(C[C@@H]1C(=O)O)(F)F

Technology Process of (R)-1-(Tert-butoxycarbonyl)-4,4-difluoropyrrolidine-2-carboxylic acid

There total 7 articles about (R)-1-(Tert-butoxycarbonyl)-4,4-difluoropyrrolidine-2-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:

methyl (R)-1-tert-butoxycarbonyl-4,4-difluoropyrrolidine-2-carboxylate (647857-74-7) → (R)-N-(tert-butoxycarbonyl)-4,4-difluoropyrrolidine-2-carboxylic acid (536747-87-2)

Guidance literature:

methyl (R)-1-tert-butoxycarbonyl-4,4-difluoropyrrolidine-2-carboxylate; With water; sodium hydroxide; In tetrahydrofuran; for 3h;

With hydrogenchloride; In water; pH=3;

Reference yield:

(2R,4R)-1-tert-butyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate (114676-69-6) → (R)-N-(tert-butoxycarbonyl)-4,4-difluoropyrrolidine-2-carboxylic acid (536747-87-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: triethylamine; sulfur trioxide pyridine complex / dimethyl sulfoxide / 1 h / 20 °C / Cooling with ice

2.1: (bis-(2-methoxyethyl)amino)sulfur trufluoride / dichloromethane / -78 - 20 °C

3.1: sodium hydroxide; water / tetrahydrofuran / 3 h

3.2: pH 3

With water; sulfur trioxide pyridine complex; triethylamine; sodium hydroxide; (bis-(2-methoxyethyl)amino)sulfur trufluoride; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide;

Reference yield:

(R)-4-oxo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (256487-77-1) → (R)-N-(tert-butoxycarbonyl)-4,4-difluoropyrrolidine-2-carboxylic acid (536747-87-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: (bis-(2-methoxyethyl)amino)sulfur trufluoride / dichloromethane / -78 - 20 °C

2.1: sodium hydroxide; water / tetrahydrofuran / 3 h

2.2: pH 3

With water; sodium hydroxide; (bis-(2-methoxyethyl)amino)sulfur trufluoride; In tetrahydrofuran; dichloromethane;

upstream raw materials:

(2R,4R)-4-hydroxy-2-methoxycarbonylpyrrolidine hydrochloride

(2R,4R)-1-tert-butyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate

cis-hydroxy-D-proline

(R)-4-oxo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Refernces

• 1、 -. "OXADIAZOLE COMPOUNDS WHICH INHIBIT BETA-SECRETASE ACTIVITY AND METHODS OF USE THEREOF". . . Retrieved 2012/05/05.
• 2、 -. "COMPOUNDS CONTAINING FUSED RINGS WHICH INHIBIT BETA-SECRETASE ACTIVITY AND METHODS OF USE THEREOF". . . Retrieved 2011/11/01.