Sodium borohydride → 11beta-Fluoro-7alpha-{5-[(3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-hexadecafluoro-dec-2-enyl)-methyl-amino]-pentyl}-estra-1,3,5(10)-triene-3,17-diol

HRID 1837254Notes

Reaction equation

HRID 1837254 reaction equation
[F:1][C@H:2]1[CH2:19][C@@:17]2([CH3:18])[C@@H:13]([CH2:14][CH2:15][C:16]2=[O:20])[C@H:12]2[C@H:3]1[C:4]1[CH:5]=[CH:6][C:7]([OH:54])=[CH:8][C:9]=1[CH2:10][C@H:11]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][N:26]([CH2:28][CH:29]=[C:30]([F:53])[C:31]([F:52])([F:51])[C:32]([F:50])([F:49])[C:33]([F:48])([F:47])[C:34]([F:46])([F:45])[C:35]([F:44])([F:43])[C:36]([F:42])([F:41])[C:37]([F:40])([F:39])[F:38])[CH3:27].[BH4-].[Na+]>CO>[F:1][C@H:2]1[CH2:19][C@@:17]2([CH3:18])[C@@H:13]([CH2:14][CH2:15][CH:16]2[OH:20])[C@H:12]2[C@H:3]1[C:4]1[CH:5]=[CH:6][C:7]([OH:54])=[CH:8][C:9]=1[CH2:10][C@H:11]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][N:26]([CH2:28][CH:29]=[C:30]([F:53])[C:31]([F:51])([F:52])[C:32]([F:49])([F:50])[C:33]([F:47])([F:48])[C:34]([F:45])([F:46])[C:35]([F:43])([F:44])[C:36]([F:41])([F:42])[C:37]([F:38])([F:39])[F:40])[CH3:27]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86587649HCID 86587649, compound

Product 1

HCID 8658765011beta-Fluoro-7alpha-{5-[(3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-hexadecafluoro-dec-2-enyl)-methyl-amino]-pentyl}-estra-1,3,5(10)-triene-3,17-diolYield 11.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.1 g of 11β-fluoro-7α-{5-[(3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-hexadecafluoro-dec-2-enyl)-methyl-amino]-pentyl}-3-hydroxy-estra-1,3,5(10)-trien-17-one is dissolved in 10 ml of methanol and carefully mixed with 148 mg of sodium borohydride. After 15 minutes of stirring at room temperature, the batch is added to saturated common salt solution, extracted with methylene chloride, dried on magnesium sulfate and concentrated by evaporation in a vacuum. After the crude product is chromatographed on silica gel with a hexane-ethyl acetate gradient and an ethyl acetate-acetone gradient, 127 mg of 11β-fluoro-7α-{5-[(3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-hexadecafluoro-dec-2-enyl)-methyl-amino]-pentyl}-estra-1,3,5(10)-triene-3,17-diol is obtained as a foam, [α]D=+35° (c=0.5 in CHCl3).

Workup

  1. additionthe batch is added to saturated common salt solution
  2. extractionextracted with methylene chloride
  3. customdried on magnesium sulfate
  4. concentrationconcentrated by evaporation in a vacuum
  5. customAfter the crude product is chromatographed on silica gel with a hexane-ethyl acetate gradient

Sources & evidence

ORD record
ord-9a893c68f489410893261b16be65d184
Source dataset
uspto-grants-2004_08
Patent number
US06780855B2

Reaction notes

Loading…