(2S,3aR,7aS)-Ethyl 1-((S)-1-phenylethyl)octahydro-1H-indole-2-carboxylate → (2S,3aR,7aS)-Ethyl octahydro-1H-indole-2-carboxylate

HRID 2065935Notes

Reaction equation

C1([C@@H]([N:9]2[C@@H:17]3[C@H:12]([CH2:13][CH2:14][CH2:15][CH2:16]3)[CH2:11][C@H:10]2[C:18]([O:20][CH2:21][CH3:22])=[O:19])C)C=CC=CC=1>[Pd].C(O)C>[NH:9]1[C@@H:17]2[C@H:12]([CH2:13][CH2:14][CH2:15][CH2:16]2)[CH2:11][C@H:10]1[C:18]([O:20][CH2:21][CH3:22])=[O:19]

Participants

Conditions

Temperature: 60 °C

Procedure

5% palladium on carbon (0.27 g) was added to a solution of (2S,3aR,7aS)-ethyl 1-((S)-1-phenylethyl)octahydro-1H-indole-2-carboxylate (15) (2.7 g) in ethanol (20 mL) and the mixture was heated at 60° C. under hydrogen (14.5 psi) atmosphere for NLT 3 hours. The catalyst was filtered and washed with fresh ethanol (15 mL). The combined filtrate was concentrated under vacuum to afford 1.93 g of (2S,3aR,7aS)-Ethyl octahydro-1H-indole-2-carboxylate (16) as a viscous oil.

Workup

filtrationThe catalyst was filtered
washwashed with fresh ethanol (15 mL)
concentrationThe combined filtrate was concentrated under vacuum

Sources & evidence

ORD record: ord-7376d6d4730b49cf9d3bf46be26959e4
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08288565B2

Reaction notes

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