Water → HCID 86759518, compound

HRID 1837277Notes

Reaction equation

HRID 1837277 reaction equation
[F:1][C@H:2]1[CH2:39][C@@:17]2([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][S:28][CH2:29][CH2:30][CH2:31][C:32]([F:38])([F:37])[C:33]([F:36])([F:35])[F:34])[C@@H:13]([CH2:14][CH2:15][C:16]2=[O:40])[C@H:12]2[C@H:3]1[C:4]1[CH:5]=[CH:6][C:7]([O:41][CH:42]3[CH2:47][CH2:46][CH2:45][CH2:44][O:43]3)=[CH:8][C:9]=1[CH2:10][CH2:11]2.O1CCCC1.O.[BH4-].[Na+]>CO.C(OCC)(=O)C>[F:1][C@H:2]1[CH2:39][C@@:17]2([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][S:28][CH2:29][CH2:30][CH2:31][C:32]([F:38])([F:37])[C:33]([F:34])([F:35])[F:36])[C@@H:13]([CH2:14][CH2:15][C@@H:16]2[OH:40])[C@H:12]2[C@H:3]1[C:4]1[CH:5]=[CH:6][C:7]([O:41][CH:42]3[CH2:47][CH2:46][CH2:45][CH2:44][O:43]3)=[CH:8][C:9]=1[CH2:10][CH2:11]2

Participants

7

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 86759519HCID 86759519, compound

Product 1

HCID 86759518HCID 86759518, compoundYield 81.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

2.2 g of 11β-fluoro-[9-(4,4,5,5,5-pentafluoropentylthio)-nonyl]-3-(tetrahydropyran-2-yloxy)-estra-1,3,5(10)-triene-17-one in a mixture of 45 ml of methanol, 7 ml of tetrahydrofuran and 4.5 ml of water is mixed in portions with 450 mg of sodium borohydride at 0° C. After 45 minutes, it is diluted with ethyl acetate, washed with water, dried and concentrated by evaporation. Chromatography of the crude product on silica gel with a hexane-ethyl acetate gradient yields 1.8 g of 11β-fluoro-[9-(4,4,5,5,5-pentafluoropentylthio)-nonyl]-3-(tetrahydropyran-2-yloxy)-estra-1,3,5(10)-trien-17β-ol as an oil.

Workup

  1. washwashed with water
  2. customdried
  3. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-636473aaf23247b5b924bcc8e627dd4b
Source dataset
uspto-grants-2004_08
Patent number
US06780855B2

Reaction notes

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