N-BOC-4,4-difluoro-L-proline

Base Information

• Chemical Name: N-BOC-4,4-difluoro-L-proline
• CAS No.: 203866-15-3
• Molecular Formula: C10H15F2NO4
• Molecular Weight: 251.23
• Hs Code.: 29339900
• Mol file: 203866-15-3.mol

Synonyms:1,2-Pyrrolidinedicarboxylicacid, 4,4-difluoro-, 1-(1,1-dimethylethyl) ester, (S)-;(2S)-1-(tert-Butoxycarbonyl)-4,4-difluoro-2-pyrrolidinecarboxylic acid;(2S)-1-tert-Butoxycarbonyl-4,4-difluoropyrrolidine-2-carboxylic acid;

Chemical Property of N-BOC-4,4-difluoro-L-proline

Chemical Property:

• Vapor Pressure: 1.58E-05mmHg at 25°C
• Melting Point: 120-124 °C
• Refractive Index: 1.474
• Boiling Point: 340.386 °C at 760 mmHg
• PKA: 3.06±0.40(Predicted)
• Flash Point: 159.66 °C
• PSA: 66.84000
• Density: 1.312 g/cm³
• LogP: 1.65360
• Storage Temp.: Store at 0-5°C

Purity/Quality:

98%, ^*data from raw suppliers

N-Boc-4,4-Difluoro-L-proline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Uses: N-Boc-4,4-difluoro-L-proline is a reagent used in the preparation of structure-activity relationship and pharmacokinetics of pyrrolotriazines as pan-Aurora kinase inhibitors and anti tumor agents.

Technology Process of N-BOC-4,4-difluoro-L-proline

There total 11 articles about N-BOC-4,4-difluoro-L-proline 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: 99.0%

1-tert-butyl 2-methyl (2S)-4,4-difluoropyrrolidine-1,2-dicarboxylate (203866-17-5) → 1-(tert-butoxycarbonyl)-4,4-difluoro-L-proline (203866-15-3)

Guidance literature:

1-tert-butyl 2-methyl (2S)-4,4-difluoropyrrolidine-1,2-dicarboxylate; With water; sodium hydroxide; In tetrahydrofuran; methanol; at 20 ℃; for 1h;

With hydrogenchloride; In water;

Reference yield: 95.0%

(S)-2-benzyl 1-tert-butyl 4,4-difluoropyrrolidine-1,2-dicarboxylate → 1-(tert-butoxycarbonyl)-4,4-difluoro-L-proline (203866-15-3)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethanol; for 2h;

Reference yield:

(S)-1-tert-butyl 2-methyl 4-oxopyrrolidine-1,2-dicarboxylate (102195-80-2) → 1-(tert-butoxycarbonyl)-4,4-difluoro-L-proline (203866-15-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 72 percent / DAST / CH₂Cl₂ / -78 - 20 °C

2: 92 percent / aq. NaOH / tetrahydrofuran / 1 h

With sodium hydroxide; 4,4'-diaminostilbene-2,2'-disulfonic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.bmc.2005.11.058

upstream raw materials:

1-tert-butyl 2-methyl (2S)-4,4-difluoropyrrolidine-1,2-dicarboxylate

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

(S)-1-tert-butyl 2-methyl 4-oxopyrrolidine-1,2-dicarboxylate

di-tert-butyl dicarbonate

Downstream raw materials:

(S)-4,4-difluoro-pyrrolidine-2-carboxylic acid

(S)-tert-butyl 2-(2-carbamoyl-4,4-difluoropyrrolidin-1-yl)-2-oxoethylcarbamate

tert-butyl (S)-(2-(2-cyano-4,4-difluoropyrrolidin-1-yl)-2-oxoethyl)carbamate

(S)-1-(2-aminoacetyl)-4,4-difluoropyrrolidine-2-carbonitrile hydrochloride

Refernces

• 1、 -. "As hepatitis c inhibitor spiro compound and its use in medicine". Paragraph 1612; 1627; 1628. . Retrieved 2017/12/28.
• 2、 -. "NOVEL COMPOUNDS USEFUL FOR THE TREATMENT OF BACTERIAL INFECTIOUS DISEASES". Paragraph 0303. . Retrieved 2016/10/31.