Cyclopentanol → HCID 10269921, compound

HRID 1370469Notes

Reaction equation

[CH:1]1([O:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:13]2[C:14]3[C@@H:15]4[CH2:26][CH2:25][NH:24][CH2:23][CH2:22][C@@H:16]4[NH:17][C:18]=3[CH:19]=[CH:20][CH:21]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:27]1(O)CCCC1>>[CH:1]1([O:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:13]2[C:14]3[C:15]4[CH2:26][CH2:25][NH:24][CH2:23][CH2:22][C:16]=4[NH:17][C:18]=3[CH:19]=[CH:20][CH:21]=2)[CH2:27][CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

Reactant 2

HCID 7298Cyclopentanol

HCID 69795958HCID 69795958, compound

Product 1

HCID 10269921HCID 10269921, compound

Procedure

Following the procedure for the preparation of (5aS*,10bS*)-10-[2-(cyclopentyloxy)phenyl]-1,2,3,4,5,5a,6,10b-octahydroazepino[4,5-b]indole and substituting cyclohexanol for cyclopentanol while making non-critical variations the title compound was obtained as 278 mg (32%) of a white foam: 1H NMR (400 MHz, CDCl3) δ 7.84 (br s, 1H), 7.35-7.26 (m, 3H), 7.15-7.11 (m, 1H), 7.04-7.01 (m, 2H), 6.95 (d, J=7.2 Hz, 1H), 4.08-4.06 (m, 1H), 3.09-3.07 (m, 2H), 2.97-2.96 (m, 2H), 2.85-2.83 (m, 2H), 2.47-2.37 (m, 2H), 1.90 (m, 2H), 1.71 (m, 2H), 1.51 (m, 2H), 1.41 (m, 2H), 1.15 (m, 3H); HRMS (FAB) calcd 3for C24H28N2O+H1: 361.2280 found 361.2270.

Sources & evidence

ORD record: ord-18682f068071447eb7ac10a8b8d5cf37
Source dataset: uspto-grants-2003_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06583135B2

Reaction notes

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