N-t-butoxycarbonyl-(2-cyanophenyl)alanine → (S)-N-t-butyloxycarbonyl(2-aminomethylphenyl)alanine

HRID 31141Notes

Reaction equation

HRID 31141 reaction equation
[C:1]([O:5][C:6]([N:8]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]#[N:21])[C@H:9]([C:11]([OH:13])=[O:12])[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2]>[Ni].CO>[C:1]([O:5][C:6]([N:8]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:20][NH2:21])[C@H:9]([C:11]([OH:13])=[O:12])[CH3:10])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 54403898N-t-butoxycarbonyl-(2-cyanophenyl)alanine

Product 1

HCID 69197459(S)-N-t-butyloxycarbonyl(2-aminomethylphenyl)alanineYield 40%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of (S)-N-t-butyloxycarbonyl(2-cyanophenyl)alanine (1.0 g), Raney® Nickel (1.0 g), and methanol (20 mL) was hydrogenated in a Parr apparatus at 50 psi for 60 h at room temperature. The catalyst was filtered and rinsed with methanol (20 mL three times). The combined filtrate and rinses were evaporated under vacuum, and the resulting residue was triturated with diethyl ether (30 mL five times) to obtain (S)-N-t-butyloxycarbonyl(2-aminomethylphenyl)alanine (406 mg).

Workup

  1. filtrationThe catalyst was filtered
  2. washrinsed with methanol (20 mL three times)
  3. customThe combined filtrate and rinses were evaporated under vacuum
  4. customthe resulting residue was triturated with diethyl ether (30 mL five times)

Sources & evidence

ORD record
ord-9684b58c14ac44ffb719e9661537e5c5
Source dataset
uspto-grants-2008_09
Patent number
US07425550B2

Reaction notes

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