2-(benzyloxy-carbonyl)-N-tert.butyl-decahydro-(4aS,8aS)-isoquinoline-3(S)-carboxamide → (3S,4aS,8aS)-N-(tert-Butyl)decahydroisoquinoline-3-carboxamide
Reaction equation
C(OC([N:11]1[C@H:20]([C:21]([NH:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:19][C@H:18]2[C@H:13]([CH2:14][CH2:15][CH2:16][CH2:17]2)[CH2:12]1)=O)C1C=CC=CC=1>C(O)C.[Pd]>[C:24]([NH:23][C:21]([C@@H:20]1[CH2:19][C@H:18]2[C@H:13]([CH2:14][CH2:15][CH2:16][CH2:17]2)[CH2:12][NH:11]1)=[O:22])([CH3:27])([CH3:25])[CH3:26]Participants
4
Procedure
A solution of 0.689 g (1.85 mmol) of 2-(benzyloxy-carbonyl)-N-tert.butyl-decahydro-(4aS,8aS)-isoquinoline-3(S)-carboxamide in 20 ml of ethanol was hydrogenated in the presence of 0.01 g of 10% palladium-on-carbon at room temperature and under atmospheric pressure for 18 hours. The catalyst was removed by filtration and the solvent was removed by evaporation to give 1.85 mmol of N-tert.butyl-decahydro-(4aS,8aS)-isoquinoline-3(S)-carboxamide as a clear oil: MS: m/e 239 [M+H]+, which was used in the next step without further purification.
Workup
- customThe catalyst was removed by filtration
- customthe solvent was removed by evaporation
Sources & evidence
- ORD record
- ord-54587553e3a24bb08f74588d4bb369b7
- Source dataset
- uspto-grants-1996_01
- Patent number
- US05488115
Reaction notes
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