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

HRID 2223345Notes

Reaction equation

HRID 2223345 reaction equation
[CH3:1][NH:2][CH3:3].Br[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C@H:10]1[CH2:27][C@@:25]2([CH3:26])[C@@H:21]([CH2:22][CH2:23][C@@H:24]2[OH:28])[C@@:20]2([CH:29]=[CH2:30])[C@H:11]1[C:12]1[CH:13]=[CH:14][C:15]([OH:31])=[CH:16][C:17]=1[CH2:18][CH2:19]2>>[CH3:1][N:2]([CH3:3])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C@H:10]1[CH2:27][C@@:25]2([CH3:26])[C@@H:21]([CH2:22][CH2:23][C@@H:24]2[OH:28])[C@@:20]2([CH:29]=[CH2:30])[C@H:11]1[C:12]1[CH:13]=[CH:14][C:15]([OH:31])=[CH:16][C:17]=1[CH2:18][CH2:19]2

Participants

3

Reactant 2

HCID 674DimethylamineHCID 1213654111beta-(5-Bromopentyl)-8-vinyl-estra-1,3,5(10)-triene-3,17beta-diol

Product 1

HCID 1213654311beta-[5-(Dimethylamino)pentyl]-8-vinylestra-1,3,5(10)-triene-3,17beta-diol

Procedure

In the reaction with dimethylamine (2 M in tetrahydrofuran, 10 equivalents) analogously to instructions 17.2, 30 mg of bromide 30a yields 12 mg of amine 32a as a colorless foam (GC-MS: m/z theor.: 411, pract.: 411).

Sources & evidence

ORD record
ord-72d67df3a32f457c9ae490d5888d3231
Source dataset
uspto-grants-2008_05
Patent number
US07375098B2

Reaction notes

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