(s)-Tert-butyl 2-(2-bromoacetyl)pyrrolidine-1-carboxylate

Base Information

• Chemical Name: (s)-Tert-butyl 2-(2-bromoacetyl)pyrrolidine-1-carboxylate
• CAS No.: 152665-75-3
• Molecular Formula: C₁₁H₁₈BrNO₃
• Molecular Weight: 292.173
• European Community (EC) Number: 859-567-5
• Mol file: 152665-75-3.mol

Synonyms:152665-75-3;(s)-tert-butyl 2-(2-bromoacetyl)pyrrolidine-1-carboxylate;TERT-BUTYL (2S)-2-(2-BROMOACETYL)PYRROLIDINE-1-CARBOXYLATE;SCHEMBL6941435;EN300-5082439

Chemical Property of (s)-Tert-butyl 2-(2-bromoacetyl)pyrrolidine-1-carboxylate

Chemical Property:

• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 291.04701
• Heavy Atom Count: 16
• Complexity: 285

Purity/Quality:

(s)-Tert-butyl2-(2-bromoacetyl)pyrrolidine-1-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CCCC1C(=O)CBr
• Isomeric SMILES: CC(C)(C)OC(=O)N1CCC[C@H]1C(=O)CBr

Technology Process of (s)-Tert-butyl 2-(2-bromoacetyl)pyrrolidine-1-carboxylate

There total 4 articles about (s)-Tert-butyl 2-(2-bromoacetyl)pyrrolidine-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: 71.0%

tert-butyl (S)-2-(diazoacetyl)pyrrolidine-1-carboxylate (101130-03-4) → (S)-2-(2-bromoacetyl)pyrrolidine-1-carboxylic acid tert-butyl ester (152665-75-3)

Guidance literature:

With hydrogen bromide; In diethyl ether; water; at 0 - 20 ℃; for 1.5h;

DOI:10.1016/j.bmcl.2008.12.002

Reference yield: 66.0%

1-(tert-butoxycarbonyl)-L-proline (15761-39-4,59433-50-0) + diazomethyl-trimethyl-silane (18107-18-1) → (S)-2-(2-bromoacetyl)pyrrolidine-1-carboxylic acid tert-butyl ester (152665-75-3)

Guidance literature:

1-(tert-butoxycarbonyl)-L-proline; With N-ethyl-N,N-diisopropylamine; isobutyl chloroformate; In tetrahydrofuran; at 0 ℃; for 4h; Inert atmosphere;

diazomethyl-trimethyl-silane; In tetrahydrofuran; hexane; acetonitrile; at 0 - 20 ℃; for 3.5h; Inert atmosphere;

With hydrogen bromide; acetic acid; In ethyl acetate; at -55 - -25 ℃; for 2.5h; Inert atmosphere;

DOI:10.1002/cmdc.201900618

Reference yield:

1-(tert-butoxycarbonyl)-L-proline (15761-39-4,59433-50-0) → (S)-2-(2-bromoacetyl)pyrrolidine-1-carboxylic acid tert-butyl ester (152665-75-3)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine / tetrahydrofuran / 0.25 h / -25 °C

2: tetrahydrofuran; diethyl ether / -15 °C

3: hydrogen bromide / tetrahydrofuran; water / 0.08 h / 20 °C

With hydrogen bromide; triethylamine; In tetrahydrofuran; diethyl ether; water;

DOI:10.2174/092986612799363172

upstream raw materials:

tert-butyl (S)-2-(diazoacetyl)pyrrolidine-1-carboxylate

1-(tert-butoxycarbonyl)-L-proline

diazomethyl-trimethyl-silane

Downstream raw materials:

C₂₅H₃₂N₂O₃

(2R,2'S)-2-(1'-methyl-2'-pyrrolidinyl)-7-phenyl-1,4-benzodioxane

(2S,2'S)-2-(1'-methyl-2'-pyrrolidinyl)-7-phenyl-1,4-benzodioxane

1-(1'-Boc-2'-pyrrolidinyl)-2-(o-benzyloxy-p-hydroxymethylphenoxy)ethanol