Methanol → (2S)-2-Amino-1-(1-pyrrolidinyl)-1-butanone

HRID 1366435Notes

Reaction equation

HRID 1366435 reaction equation
[N:1]1([C:6]([C@@H:8]([NH:11]C(=O)OCC2C=CC=CC=2)[CH2:9][CH3:10])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.CO>[OH-].[OH-].[Pd+2]>[N:1]1([C:6]([C@@H:8]([NH2:11])[CH2:9][CH3:10])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 887MethanolHCID 15130882HCID 15130882, compound

Product 1

HCID 58293418(2S)-2-Amino-1-(1-pyrrolidinyl)-1-butanoneYield 97%

Reagents, catalysts & solvents 1

HCID 9942167Palladium hydroxideCatalyst

Procedure

Phenylmethyl [(1S)-1-(1-pyrrolidinylcarbonyl)propyl]carbamate (J. Med. Chem., 1991, 34, 3149-58) was dissolved in methanol (20 mL) (559 mg, 1.9 mmol). Pd(OH)2 (140 mg) was added, and the resulting suspension was stirred under a hydrogen balloon until the deprotection was complete. Filtration of the catalyst and evaporation of the solvent yielded [(1S)-1-(1-pyrrolidinylcarbonyl)propyl]amine (291 mg, 97%).

Workup

  1. filtrationFiltration of the catalyst and evaporation of the solvent

Sources & evidence

ORD record
ord-1a17f13c5aa34ec686eaf1c0840c4e4a
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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