3-Benzyloxycarbonylamino-5,5-dimethyl-octanoic acid tert-butyl ester → (S)-3-Amino-5,5-dimethyl-octanoic acid tert-butyl ester

HRID 2216679Notes

Reaction equation

HRID 2216679 reaction equation
[C:1]([O:5][C:6](=[O:27])[CH2:7][CH:8]([NH:16]C(OCC1C=CC=CC=1)=O)[CH2:9][C:10]([CH3:15])([CH3:14])[CH2:11][CH2:12][CH3:13])([CH3:4])([CH3:3])[CH3:2]>[Pd]>[C:1]([O:5][C:6](=[O:27])[CH2:7][C@@H:8]([NH2:16])[CH2:9][C:10]([CH3:15])([CH3:14])[CH2:11][CH2:12][CH3:13])([CH3:3])([CH3:2])[CH3:4]

Participants

3

Reactant 1

HCID 688548473-Benzyloxycarbonylamino-5,5-dimethyl-octanoic acid tert-butyl ester

Product 1

HCID 86589982(S)-3-Amino-5,5-dimethyl-octanoic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

According to example 1, 1.63 g of 3-benzyloxycarbonylamino-5,5-dimethyl-octanoic acid tert-butyl ester and 0.2 g of 20% Pd/C furnished the title compound. 1HNMR (400 MHz; CDCl3): 0.84–0.89 (m, 9H), 1.13–1.39 (m, 6H), 1.43 (s, 9H), 2.25 (dd, 1H, J=8.4 Hz, 15.6 Hz), 2.35 (dd, 1H, J=4.4 Hz, 15.6 Hz), 2.79 (s, br, 2H), 3.25–3.35 (m, 1H). MS, m/z, 244.2 (M+1)+.

Sources & evidence

ORD record
ord-1dcbede4781d4b919fbde77dbaa3cc72
Source dataset
uspto-grants-2006_09
Patent number
US07112610B2

Reaction notes

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