Diethyl Ether → Benzyl 3-acetamido-4-hydroxypyrrolidine-1-carboxylate

HRID 400451Notes

Reaction equation

HRID 400451 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[NH2:8][CH:9]1[CH:13]([OH:14])[CH2:12][N:11]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH2:10]1.C(OCC)C>ClCCl>[C:1]([NH:8][CH:9]1[CH:13]([OH:14])[CH2:12][N:11]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH2:10]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 7918Acetic AnhydrideHCID 17917965Benzyl 3-amino-4-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 86686049Benzyl 3-acetamido-4-hydroxypyrrolidine-1-carboxylateYield 90.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3.24 g acetic anhydride was added to 7.1 g benzyl 3-amino-4-hydroxypyrrolidine-1-carboxylate in 100 mL dichlormethane at 0-5° C. The mixture was stirred 2 h at RT, 100 mL diethylether was added and the mixture was stirred for 15 min. The precipitate was filtered to give 7.6 g of the desired product.

Workup

  1. stirringthe mixture was stirred for 15 min
  2. filtrationThe precipitate was filtered

Sources & evidence

ORD record
ord-5390c99a64d24fc19fc814ee9fa96953
Source dataset
uspto-grants-2014_06
Patent number
US08741892B2

Reaction notes

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