1-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acid → 3beta-(N-(tert-Butoxycarbonyl)piperidin-4-ylcarbonyloxy)androstane-6,17-dione

HRID 42127Notes

Reaction equation

HRID 42127 reaction equation
[OH:1][C@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[CH:4]([C:5](=[O:22])[CH2:6][C@@H:7]3[C@@H:16]2[CH2:15][CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][CH2:10][C:11]2=[O:21])[CH2:3]1.[C:23]([O:27][C:28]([N:30]1[CH2:35][CH2:34][CH:33]([C:36](O)=[O:37])[CH2:32][CH2:31]1)=[O:29])([CH3:26])([CH3:25])[CH3:24]>>[C:23]([O:27][C:28]([N:30]1[CH2:35][CH2:34][CH:33]([C:36]([O:1][C@H:2]2[CH2:19][CH2:18][C@@:17]3([CH3:20])[CH:4]([C:5](=[O:22])[CH2:6][C@@H:7]4[C@@H:16]3[CH2:15][CH2:14][C@@:12]3([CH3:13])[C@H:8]4[CH2:9][CH2:10][C:11]3=[O:21])[CH2:3]2)=[O:37])[CH2:32][CH2:31]1)=[O:29])([CH3:26])([CH3:25])[CH3:24]

Participants

3

Reactant 2

HCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 690126423beta-Hydroxy-5alpha-androstan-6,17-dione

Product 1

HCID 690075523beta-(N-(tert-Butoxycarbonyl)piperidin-4-ylcarbonyloxy)androstane-6,17-dioneYield 62%

Procedure

Prepared in 62% yield from 3β-hydroxyandrostane-6,17-dione and 1-(tert-butoxycarbonyl)-4-piperidinecarboxylic acid by the procedure described in Prepn. 43. 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ 4.65 (1H, m), 3.60-1.20 (29H, m), 1.35 (9H, s), 0.78 (3H, s), 0.69 (3H, s).

Sources & evidence

ORD record
ord-1d14a398c4934b3d94989ff830c09e66
Source dataset
uspto-grants-2013_09
Patent number
US08536160B2

Reaction notes

Loading…