L-Phenylglycine → (alphaS)-alpha-Aminocyclohexaneacetic acid

HRID 1742204Notes

Reaction equation

HRID 1742204 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([C@H:7]([NH2:11])[C:8]([OH:10])=[O:9])=[CH:3][CH:2]=1>C(O)(=O)C.O=[Pt]=O>[NH2:11][C@@H:7]([CH:4]1[CH2:5][CH2:6][CH2:1][CH2:2][CH2:3]1)[C:8]([OH:10])=[O:9]

Participants

4

Reactant 1

HCID 99291L-Phenylglycine

Product 1

HCID 736848(alphaS)-alpha-Aminocyclohexaneacetic acidYield 94%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

L-Phenylglycine (8.04 g, 53 mmol) was reduced by catalytic hydrogenation using PtO2 in 80% acetic acid (HOAc) (200 mL). The catalyst was removed by filtration and the HOAc removed under reduced pressure to afford the title compound as a white solid (7.8 g, 94%). The 300 MHz 1H NMR spectrum was found to be consistent with the proposed structure.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe HOAc removed under reduced pressure

Sources & evidence

ORD record
ord-e53c6e87187a4405aa1d64ff3b823b56
Source dataset
uspto-grants-1994_08
Patent number
US05338726

Reaction notes

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