N-[(2E)-2-(1,2,6,7-tetrahydro-8H-cyclopenta[b]furo[3,2-d]pyridin-8-ylidene)ethyl]propanamide → N-[2-(1,6,7,8-tetrahydro-2H-cyclopenta[b]furo[3,2-d]pyridin-8-yl)ethyl]propanamide

HRID 2389941Notes

Reaction equation

[CH2:1]1[C:5]2=[C:6]3[C:7]([CH2:10][CH2:11]/[C:12]/3=[CH:13]\[CH2:14][NH:15][C:16](=[O:19])[CH2:17][CH3:18])=[N:8][CH:9]=[C:4]2[O:3][CH2:2]1>CO.[C].[Pd]>[CH2:1]1[C:5]2=[C:6]3[CH:12]([CH2:13][CH2:14][NH:15][C:16](=[O:19])[CH2:17][CH3:18])[CH2:11][CH2:10][C:7]3=[N:8][CH:9]=[C:4]2[O:3][CH2:2]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of N-[(2E)-2-(1,2,6,7-tetrahydro-8H-cyclopenta[b]furo[3,2-d]pyridin-8-ylidene)ethyl]propanamide (65.0 mg, 0.252 mmol) in methanol (1.3 mL) was added palladium-carbon powder (13 mg), and the mixture was stirred at 50° C. for 6 hr under a hydrogen atmosphere. The catalyst was filtered off, and the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=50/50→100/0) to give the title compound (39.5 mg, yield 60%).

Workup

filtrationThe catalyst was filtered off
customthe filtrate was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=50/50→100/0)

Sources & evidence

ORD record: ord-1d2480bba4ff4d7bae901be3c65700fa
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273761B2

Reaction notes

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