Sodium borohydride → HCID 10740169, compound

HRID 1080635Notes

Reaction equation

HRID 1080635 reaction equation
[C:1]([O:4][C@H:5]1[CH2:26][CH2:25][C@@:24]2([CH3:27])[C@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:23]2[CH2:22][CH2:21][C@@:20]2([CH3:28])[C@:11]3([OH:29])[CH2:12][CH2:13][C@@H:14]2[CH:15]=[CH:16][N+:17]([O-:19])=[O:18])[CH2:6]1)(=[O:3])[CH3:2].[BH4-].[Na+].P([O-])(O)(O)=O.[Na+]>C(OCC)C.C(O)C>[C:1]([O:4][C@H:5]1[CH2:26][CH2:25][C@@:24]2([CH3:27])[C@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:23]2[CH2:22][CH2:21][C@@:20]2([CH3:28])[C@:11]3([OH:29])[CH2:12][CH2:13][C@@H:14]2[CH2:15][CH2:16][N+:17]([O-:19])=[O:18])[CH2:6]1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 4311764Sodium borohydrideHCID 23672064Monosodium phosphateHCID 70045315HCID 70045315, compound

Product 1

HCID 10740169HCID 10740169, compoundYield 96.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 13.86 g of 3β-acetoxy-21-nitro-5β-pregn-20-en-14β-ol (Eberlein W. et al., Chem. Ber., 1974, 107, 1275) in 440 ml of diethyl ether and 440 ml of ethanol, 2.86 g NaBH4 were added at room temperature. After 1 hr. the mixture was neutralized with aqueous sodium dihydrogenphosphate and extracted with methylene chloride. The organic layer was washed with water, dried over anhydrous sodium sulfate and evaporated to dryness to give 13.40 g of 3β-acetoxy-21-nitro-5β-pregnane-14β-ol.

Workup

  1. extractionextracted with methylene chloride
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-625b732f5f044ad28e1579a0c547ec43
Source dataset
uspto-grants-1996_12
Patent number
US05583127

Reaction notes

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