Water → HCID 70522181, compound

HRID 1702586Notes

Reaction equation

HRID 1702586 reaction equation
[BH4-].[Na+].[C:3]([O:8][C@@H:9]1[C@@H:26]([N:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)[CH2:25][C@@:24]2([CH3:33])[C@@H:11]([CH2:12][CH2:13][C@@H:14]3[C@@H:23]2[CH2:22][CH2:21][C@@:19]2([CH3:20])[C@H:15]3[CH2:16][C@H:17]([N:35]3[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]3)[C:18]2=[O:34])[CH2:10]1)(=[O:7])[CH:4]([CH3:6])[CH3:5].O>C(Cl)Cl.CO>[C:3]([O:8][C@@H:9]1[C@@H:26]([N:27]2[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]2)[CH2:25][C@@:24]2([CH3:33])[C@@H:11]([CH2:12][CH2:13][C@@H:14]3[C@@H:23]2[CH2:22][CH2:21][C@@:19]2([CH3:20])[C@H:15]3[CH2:16][C@H:17]([N:35]3[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40]3)[C@@H:18]2[OH:34])[CH2:10]1)(=[O:7])[CH:4]([CH3:6])[CH3:5]

Participants

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 22821470HCID 22821470, compound

Product 1

HCID 70522181HCID 70522181, compoundYield 40.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Sodium borohydride (16 g) was added to a stirred solution of 3α-isobutyroxy-2β,16β-dipiperidino-5α-androstan-17-one (51.6 g) in methylene dichloride (150 ml) and methanol (150 ml) and the reaction mixture was stirred for a further hour. Water was added, the product extracted with ether, and the extract washed well with water and dried. Concentration of the ether solution yielded 2β,16β-dipiperidino-5α-androstan-3α,17β-diol 3-isobutyrate (21 g) which was recrystallised from ether.

Workup

  1. extractionthe product extracted with ether
  2. washthe extract washed well with water
  3. customdried

Sources & evidence

ORD record
ord-26b5dfe436e945e8a72cb7f91d2eeb04
Source dataset
uspto-grants-1982_09
Patent number
US04348390

Reaction notes

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