Chloroform ethanol → (1SR,3RS,4SR)-3-aminomethyl-4-methoxy-cyclopentanecarboxylic acid methyl ester hydrochloride

HRID 2244696Notes

Reaction equation

HRID 2244696 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH:8]([O:10][CH3:11])[CH:7]([C:12]#[N:13])[CH2:6]1)=[O:4].C(O)C.C(Cl)(Cl)[Cl:18]>O=[Pt]=O>[ClH:18].[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH:8]([O:10][CH3:11])[CH:7]([CH2:12][NH2:13])[CH2:6]1)=[O:4]

Participants

4

Reactant 2

HCID 21889567Chloroform ethanolHCID 68686720(1SR,3RS,4SR)-3-cyano-4-methoxy-cyclopentanecarboxylic acid methyl ester

Product 1

HCID 68686110(1SR,3RS,4SR)-3-aminomethyl-4-methoxy-cyclopentanecarboxylic acid methyl ester hydrochloride

Reagents, catalysts & solvents 1

HCID 345198Adams' catalystCatalyst

Procedure

To a stirred solution of (1SR,3RS,4SR)-3-cyano-4-methoxy-cyclopentanecarboxylic acid methyl ester (595 mg) in ethanol/chloroform 5:1 (6 ml) was added PtO2 (60 mg). The reaction mixture was hydrogenated overnight. The catalyst was filtered off and washed with MeOH. The filtrate was concentrated to give (1SR,3RS,4SR)-3-aminomethyl-4-methoxy-cyclopentanecarboxylic acid methyl ester hydrochloride (704 mg) as white amorphous semisolid. MS 188.3 ([M+H]+).

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with MeOH
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-6615fd77310b49919d5cc6b2f6ba7a40
Source dataset
uspto-grants-2010_03
Patent number
US07678917B2

Reaction notes

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