Sodium borohydride → HCID 15542228, compound

HRID 361670Notes

Reaction equation

[OH:1][C:2]1[CH:19]=[CH:18][C:17]2[C@@H:16]3[C@H:7]([C@H:8]4[C@@:12]([CH2:14][CH2:15]3)([CH3:13])[C:11](=[O:20])[CH2:10][CH2:9]4)[CH:6]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][N:26]3[CH2:30][CH2:29][CH2:28][C@H:27]3[CH2:31][S:32][CH2:33][CH2:34][CH2:35][C:36]([F:42])([F:41])[C:37]([F:40])([F:39])[F:38])[CH2:5][C:4]=2[CH:3]=1.[BH4-].[Na+]>>[F:42][C:36]([F:41])([C:37]([F:38])([F:39])[F:40])[CH2:35][CH2:34][CH2:33][S:32][CH2:31][C@@H:27]1[CH2:28][CH2:29][CH2:30][N:26]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][C@@H:6]1[CH2:5][C:4]2[CH:3]=[C:2]([OH:1])[CH:19]=[CH:18][C:17]=2[C@@H:16]2[C@@H:7]1[C@H:8]1[C@@:12]([CH2:14][CH2:15]2)([CH3:13])[C@@H:11]([OH:20])[CH2:10][CH2:9]1

Participants

Reactant 2

HCID 4311764Sodium borohydride

HCID 22941803HCID 22941803, compound

Product 1

HCID 15542228HCID 15542228, compoundYield 64.8%

Procedure

Under the conditions of Example 8, 500 mg of 3-hydroxy-7 -(5-[(2S)-2-(4,4,5,5,5-pentafluoropentylthiomethyl)-pyrrolidin-1-yl]-pentyl)-estra-1,3,5(10)-trien-17-one is reduced with 100 mg of sodium borohydride. 325 mg of the title compound is obtained as oil. [α]D22 =-8.7°(c=0.510 in methanol).

Sources & evidence

ORD record: ord-1813695a84ef4dcab60c8722b72a5fa0
Source dataset: uspto-grants-1999_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05866560

Reaction notes

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