Cyclopentanol → HCID 10268499, compound

HRID 1356352Notes

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]C[CH2:2]1.C1(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)[CH2:2][CH2:4][CH2:5]1

Participants

Reactant 2

HCID 7298Cyclopentanol

HCID 69795958HCID 69795958, compound

Product 1

HCID 10268499HCID 10268499, 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 cyclobutanol for cyclopentanol while making non-critical variations the title compound was obtained as 193 mg (37%) of a tan solid: mp 182.0-184.5° C. 1H NMR (400 MHz, CDCl3) δ 7.85 (br s, 1H), 7.35-7.28 (m, 3 H), 7.18-7.14 (m, 1H), 7.04-7.00 (m, 1H), 6.94 (d, J=7.2 Hz, 1H), 6.84 (d, J=8.2 Hz, 1H), 4.63-4.56 (m, 1H), 3.10-3.07 (m, 2H), 2.98-2.95 (m, 2H), 2.87-2.84 (m, 2H), 2.47-2.41 (m, 2H), 2.37-2.32 (m, 2H), 2.02-2.00 (m, 2H), 1.74-172 (m, 1H), 1.64-1.59 (m, 1H); HRMS (FAB) calcd for C22H24N2O+H1: 333.1967 found 333.1960.

Sources & evidence

ORD record: ord-063dfb0bb08249a49ff70c76d747d6ec
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06586421B2

Reaction notes

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