Piperidine → 11beta-[5-(1-Piperidyl)pentyl]-8-vinylestra-1,3,5(10)-triene-3,17beta-diol

HRID 2223346Notes

Reaction equation

HRID 2223346 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Br[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C@H:13]1[CH2:30][C@@:28]2([CH3:29])[C@@H:24]([CH2:25][CH2:26][C@@H:27]2[OH:31])[C@@:23]2([CH:32]=[CH2:33])[C@H:14]1[C:15]1[CH:16]=[CH:17][C:18]([OH:34])=[CH:19][C:20]=1[CH2:21][CH2:22]2>>[N:1]1([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C@H:13]2[CH2:30][C@@:28]3([CH3:29])[C@@H:24]([CH2:25][CH2:26][C@@H:27]3[OH:31])[C@@:23]3([CH:32]=[CH2:33])[C@H:14]2[C:15]2[CH:16]=[CH:17][C:18]([OH:34])=[CH:19][C:20]=2[CH2:21][CH2:22]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 8082PiperidineHCID 1213654111beta-(5-Bromopentyl)-8-vinyl-estra-1,3,5(10)-triene-3,17beta-diol

Product 1

HCID 1213654511beta-[5-(1-Piperidyl)pentyl]-8-vinylestra-1,3,5(10)-triene-3,17beta-diol

Procedure

In the reaction with piperidine (10 equivalents) analogously to instructions 17.2, 50 mg of bromide 30a yields 41 mg of amine 34a as a colorless foam (GC-MS: m/z theor.: 451, pract.: 451).

Sources & evidence

ORD record
ord-6bb0924d99fd4435be95e2f58319c200
Source dataset
uspto-grants-2008_05
Patent number
US07375098B2

Reaction notes

Loading…