(6R,7S)-7-dibenzylamino-6-ethyl-2-fluoro-9-(2,2,2-trifluoro-ethyl)-6,7-dihydro-9H-5-oxa-9-aza-benzocyclohepten-8-one → (6R,7S)-7-Amino-6-ethyl-2-fluoro-9-(2,2,2-trifluoro-ethyl)-6,7-dihydro-9H-5-oxa-9-aza-benzocyclohepten-8-one

HRID 1348664Notes

Reaction equation

HRID 1348664 reaction equation
C([N:8](CC1C=CC=CC=1)[C@@H:9]1[C:15](=[O:16])[N:14]([CH2:17][C:18]([F:21])([F:20])[F:19])[C:13]2[CH:22]=[C:23]([F:26])[CH:24]=[CH:25][C:12]=2[O:11][C@@H:10]1[CH2:27][CH3:28])C1C=CC=CC=1>CO.[Pd]>[NH2:8][C@@H:9]1[C:15](=[O:16])[N:14]([CH2:17][C:18]([F:19])([F:21])[F:20])[C:13]2[CH:22]=[C:23]([F:26])[CH:24]=[CH:25][C:12]=2[O:11][C@@H:10]1[CH2:27][CH3:28]

Participants

4

Reactant 1

HCID 21091452(6R,7S)-7-dibenzylamino-6-ethyl-2-fluoro-9-(2,2,2-trifluoro-ethyl)-6,7-dihydro-9H-5-oxa-9-aza-benzocyclohepten-8-one

Product 1

HCID 21091446(6R,7S)-7-Amino-6-ethyl-2-fluoro-9-(2,2,2-trifluoro-ethyl)-6,7-dihydro-9H-5-oxa-9-aza-benzocyclohepten-8-oneYield 66%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The title compound was prepared in 66% yield by hydrogenation of (6R,7S)-7-dibenzylamino-6-ethyl-2-fluoro-9-(2,2,2-trifluoro-ethyl)-6,7-dihydro-9H-5-oxa-9-aza-benzocyclohepten-8-one in methanol with Pd/C (10%), MS m/e (%): 307.1 (M+H+, 100).

Sources & evidence

ORD record
ord-a7acc2a5dad9482d837e127dc962bf62
Source dataset
uspto-grants-2007_05
Patent number
US07211573B2

Reaction notes

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