(R)-tert-butyl 3-bromopyrrolidine-1-carboxylate

Base Information

• Chemical Name: (R)-tert-butyl 3-bromopyrrolidine-1-carboxylate
• CAS No.: 569660-97-5
• Molecular Formula: C9H16BrNO2
• Molecular Weight: 250.13300
• Hs Code.: 2933990090
• Mol file: 569660-97-5.mol

Synonyms:HT931;(3R)-3-Bromo-1-pyrrolidinecarboxylic acid tert-butyl ester;(R)-3-Bromo-pyrrolidine-1-carboxylic acid tert-butyl ester;

Chemical Property of (R)-tert-butyl 3-bromopyrrolidine-1-carboxylate

Chemical Property:

• Boiling Point: 278℃
• PKA: -3.30±0.40(Predicted)
• Flash Point: 122℃
• PSA: 29.54000
• Density: 1.379
• LogP: 2.32860
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C

Purity/Quality:

NLT 98% ^*data from raw suppliers

(R)-1-Boc-3-Bromopyrrolidine 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: It is used as a pharmaceutical intermediate.

Technology Process of (R)-tert-butyl 3-bromopyrrolidine-1-carboxylate

There total 3 articles about (R)-tert-butyl 3-bromopyrrolidine-1-carboxylate 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: 100.0%

(R)-tert-butyl 3-hydroxypyrrolidine-1-carboxylate (109431-87-0,83220-73-9) → tert-butyl (3S)-3-bromopyrrolidine-1-carboxylate (569660-89-5,569660-97-5)

Guidance literature:

With carbon tetrabromide; triphenylphosphine; In tetrahydrofuran; at 5 ℃; for 0.0833333h;

Reference yield: 83.0%

N-(tert-butoxycarbonyl)-3-hydroxypyrrolidine (103057-44-9,83220-73-9) → 3-bromopyrrolidine-1-carboxylic acid tert-butyl ester (939793-16-5,569660-97-5)

Guidance literature:

With carbon tetrabromide; triphenylphosphine; In tetrahydrofuran; Inert atmosphere;

DOI:10.1021/jacs.6b04610

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → 3-bromopyrrolidine-1-carboxylic acid tert-butyl ester (939793-16-5,569660-97-5)

Guidance literature:

Multi-step reaction with 2 steps

1: dmap / neat (no solvent) / 20 °C

2: triphenylphosphine; carbon tetrabromide / tetrahydrofuran / 0 - 20 °C

With dmap; carbon tetrabromide; triphenylphosphine; In tetrahydrofuran; 2: |Appel Halogenation;

DOI:10.1021/acs.jmedchem.7b00316

upstream raw materials:

(R)-tert-butyl 3-hydroxypyrrolidine-1-carboxylate

N-(tert-butoxycarbonyl)-3-hydroxypyrrolidine

di-tert-butyl dicarbonate

Downstream raw materials:

tert-butyl 3-phenylpyrrolidine-1-carboxylate

C₁₅H₂₈BNO₄

tert-butyl 3-fluoropyrrolidine-1-carboxylate

tert-butyl 3-(4-bromo-1H-pyrazol-1-yl) pyrrolidine-1-carboxylate

Refernces

• 1、 Sargent, Brendon T.,Alexanian, Erik J.. "Palladium-Catalyzed Alkoxycarbonylation of Unactivated Secondary Alkyl Bromides at Low Pressure". supporting information. p. 7520 - 7523. Retrieved 2016/07/06.
• 2、 -. "BIARYL CARBOXAMIDES". Page/Page column 37. . Retrieved 2010/08/04.