Sodium borohydride → HCID 66910182, compound

HRID 910602Notes

Reaction equation

HRID 910602 reaction equation
[C:1]([O:4][C@@H:5]1[CH:22]2[C@:17]([CH3:24])([CH2:18][CH2:19][C:20](=[O:23])[CH2:21]2)[C@@H:16]2[C@H:7]([C@H:8]3[C@@:12]([CH2:14][CH2:15]2)([CH3:13])[C:11](=[O:25])[CH2:10][CH2:9]3)[CH2:6]1)(=[O:3])[CH3:2].[BH4-].[Na+]>CO>[C:1]([O:4][C@@H:5]1[CH:22]2[C@:17]([CH3:24])([CH2:18][CH2:19][C@H:20]([OH:23])[CH2:21]2)[C@@H:16]2[C@H:7]([C@H:8]3[C@@:12]([CH2:14][CH2:15]2)([CH3:13])[C@@H:11]([OH:25])[CH2:10][CH2:9]3)[CH2:6]1)(=[O:3])[CH3:2].[C:1]([O:4][C@@H:5]1[CH:22]2[C@:17]([CH3:24])([CH2:18][CH2:19][C@@H:20]([OH:23])[CH2:21]2)[C@@H:16]2[C@H:7]([C@H:8]3[C@@:12]([CH2:14][CH2:15]2)([CH3:13])[C@@H:11]([OH:25])[CH2:10][CH2:9]3)[CH2:6]1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 66910130HCID 66910130, compound

Product 2

HCID 66910147HCID 66910147, compoundHCID 66910182HCID 66910182, compoundYield 188.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 6α-acetoxyandrostane-3,17-dione (5.57 g) in MeOH (188 mL), at 0° C. under N2, NaBH4 (615 mg) was added in portions over 15 min. After stirring for 1.5 h at room temperature, the mixture was quenched by careful addition of H2O (200 mL). MeOH was evaporated and the concentrated solution was extracted with EtOAc. The combined organic extracts were washed with brine, dried over Na2SO4 and evaporated to dryness. The mixture was purified by flash chromatography (SiO2, cyclohexane/Et2O/acetone 60/20/20) to give 6α-acetoxyandrostane-3β,17β-diol and 6α-acetoxyandrostane-3α,17β-diol (90/10 mixture, 5.30 g, 95%). 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ 4.55 (m, 1H), 4.49 (bb, 1H), 4.43 (bb, 1H), 3.41 (m, 1H), 3.28 (m, 1H), 1.97 (s, 3H), 1.88-0.82 (m, 19H), 0.79 (s, 3H), 0.64 (m, 1H), 0.61 (s, 3H).

Workup

  1. customthe mixture was quenched by careful addition of H2O (200 mL)
  2. customMeOH was evaporated
  3. extractionthe concentrated solution was extracted with EtOAc
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. customevaporated to dryness
  7. customThe mixture was purified by flash chromatography (SiO2, cyclohexane/Et2O/acetone 60/20/20)

Sources & evidence

ORD record
ord-a94b7594a0cf4dd2b039e0f3164e3437
Source dataset
uspto-grants-2011_09
Patent number
US08022203B2

Reaction notes

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