Sodium borohydride → 3-Methoxy-18-methyl-1,3,5(10),15-estratetraen-17beta-ol

HRID 1650117Notes

Reaction equation

HRID 1650117 reaction equation
[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:19]2[C@@H:18]3[C@H:8]([C@H:9]4[C@@:13]([CH2:16][CH2:17]3)([CH2:14][CH3:15])[C:12](=[O:22])[CH:11]=[CH:10]4)[CH2:7][CH2:6][C:5]=2[CH:4]=1.O.O.O.O.O.O.O.[Cl-].[Ce+3].[Cl-].[Cl-].[BH4-].[Na+]>O1CCCC1.CO.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:19]2[C@@H:18]3[C@H:8]([C@H:9]4[C@@:13]([CH2:16][CH2:17]3)([CH2:14][CH3:15])[C@@H:12]([OH:22])[CH:11]=[CH:10]4)[CH2:7][CH2:6][C:5]=2[CH:4]=1

Participants

7

Reactant 3

HCID 4311764Sodium borohydrideHCID 14257189(8R,9S,13S,14S)-13-ethyl-3-methoxy-7,8,9,11,12,14-hexahydro-6H-cyclopenta[a]phenanthren-17-oneHCID 21585214Cerium trichloride heptahydrate

Product 1

HCID 142571913-Methoxy-18-methyl-1,3,5(10),15-estratetraen-17beta-olYield 95.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

4.7 g of 3-methoxy-18-methyl-1,3,5(10),15-estratetraen-17-one in 30 ml of tetrahydrofuran and 45 ml of methanol are mixed with 6.8 g of cerium(III)-chloride heptahydrate. At 0° C., 1.0 g of sodium borohydride is added, in portions. After 1 hour, the reaction mixture is put in ice/water. The precipitated product is suctioned off, dissolved in ethyl acetate, washed with water and dried. 4.5 g of 3-methoxy-18-methyl-1,3,5(10),15-estratetraen-17β-ol is obtained as a foam.

Workup

  1. washwashed with water
  2. customdried

Sources & evidence

ORD record
ord-b2d4f757bd81478e8c6e297e53c393b0
Source dataset
uspto-grants-1990_05
Patent number
US04923640

Reaction notes

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