methyl 13-cyclohexyl-6-(benzyloxycarbonyl)-5H-indolo[2,1-a][2]benzazepine-10-carboxylate → 13-cyclohexyl-10-methoxycarbonyl-6,7-dihydro-5H-indolo[2,1-a][2]benzazepine-6-carboxylic acid

HRID 1394840Notes

Reaction equation

[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:35]([O:37][CH3:38])=[O:36])=[CH:12][C:13]=3[N:14]3[CH:20]=[C:19]([C:21]([O:23]CC4C=CC=CC=4)=[O:22])[CH2:18][C:17]4[CH:31]=[CH:32][CH:33]=[CH:34][C:16]=4[C:15]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>[Pd].C1COCC1.CO>[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:35]([O:37][CH3:38])=[O:36])=[CH:12][C:13]=3[N:14]3[CH2:20][CH:19]([C:21]([OH:23])=[O:22])[CH2:18][C:17]4[CH:31]=[CH:32][CH:33]=[CH:34][C:16]=4[C:15]=23)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

Conditions

Temperature: 22 °C

Procedure

Method A: The intermediate ester (14, R=H, 53 mg, 0.13 mmol) in a 1:1 mixture of THF/MeOH (2 mL) was treated with a catalytic amount of Pd (10% on C) under hydrogen (balloon pressure). The mixture was stirred at 22° C. for 18 hr. The catalyst was removed by filtration through a fine pad of celite and the solution was concentrated in vacuo to afford the title compound as a pale tan solid (50 mg, 92%). ESI-MS m/z 418 (MH+).

Workup

customThe catalyst was removed by filtration through a fine pad of celite
concentrationthe solution was concentrated in vacuo

Sources & evidence

ORD record: ord-3814f5aacce14ab08da64c879eb05ec4
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07348425B2

Reaction notes

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