Phenylalanine amide → (2S)-3-Phenylpropane-1,2-diamine

HRID 714282Notes

Reaction equation

NC(CCC)C#N.[NH2:8][C@H:9]([C:17]([NH2:19])=O)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>[C:11]1([CH2:10][C@H:9]([NH2:8])[CH2:17][NH2:19])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

Reactant 3

HCID 445694Phenylalanine amide

HCID 101712882-Aminopentanenitrile

HCID 21226445Aluminium lithium hydride

Product 1

HCID 12699301(2S)-3-Phenylpropane-1,2-diamineYield 35%

Procedure

Following the procedure as described in Preparation 11, making variations as required to replace 2-aminopentanenitrile with L-phenylalanineamide to react with lithium aluminum hydride, (S)-3-phenylpropane-1,2-diamine was obtained as a colorless solid in 35% yield: MS (ES+) m/z 151.2 (M+1).

Workup

customas described in Preparation 11

Sources & evidence

ORD record: ord-34b84eebebbb4076b5083de9d6f058a5
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187426B2

Reaction notes

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