Benzylamine → HCID 57869945, compound

HRID 1045686Notes

Reaction equation

HRID 1045686 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10](OS(C)(=O)=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:18]([NH2:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([NH:25][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 7504BenzylamineHCID 11032777(S)-1-Boc-3-methanesulfonyloxy-pyrrolidine

Product 1

HCID 57869945HCID 57869945, compoundYield 97.1%

Procedure

A solution of (S)-3-methanesulfonyloxypyrrolidine-1-carboxylic acid tert-butyl ester (16.9 g, 57 mmol) and benzylamine (18.3 g, 171 mmol) was stirred for 4 hours at 95° C. The remaining benzylamine was evaporated off under reduced pressure and the residue was purified by silica gel column chromatography (eluent; ethyl acetate) to afford (R)-3-benzylaminopyrrolidine-1-carboxylic acid tert-butyl ester (15.3 g, 97%) as pale yellow oil.

Workup

  1. customThe remaining benzylamine was evaporated off under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (eluent; ethyl acetate)

Sources & evidence

ORD record
ord-46acf45a0a254e2eaf6501a0d521ce62
Source dataset
uspto-grants-2013_10
Patent number
US08569294B2

Reaction notes

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