Sodium borohydride → HCID 70583636, compound

HRID 1701442Notes

Reaction equation

HRID 1701442 reaction equation
C1CO[C:3]([C@@H:5]2[C@:22]3([CH3:23])[C@H:8]([C@H:9]4[C@H:19]([C:20](=[O:24])[CH2:21]3)[C@:17]3([CH3:18])[C@H:12]([CH2:13][C@H:14]([OH:25])[CH2:15][CH2:16]3)[C@H:11]([CH3:26])[CH2:10]4)[CH2:7][CH2:6]2)([CH3:4])[O:2]1.[BH4-].[Na+]>CC(O)C.O.CC(C)=O.Cl>[OH:25][C@@H:14]1[CH2:15][CH2:16][C@@:17]2([CH3:18])[C@@H:12]([C@H:11]([CH3:26])[CH2:10][C@@H:9]3[C@@H:19]2[C@@H:20]([OH:24])[CH2:21][C@@:22]2([CH3:23])[C@H:8]3[CH2:7][CH2:6][C@@H:5]2[C:3](=[O:2])[CH3:4])[CH2:13]1

Participants

7

Reactant 2

HCID 4311764Sodium borohydrideHCID 70583415HCID 70583415, compound

Product 1

HCID 70583636HCID 70583636, compoundYield 57.7%

Reagents, catalysts & solvents 4

HCID 180AcetoneSolventHCID 313Hydrochloric AcidSolventHCID 962WaterSolvent3×HCID 3776IsopropanolSolvent

Procedure

20,20-Ethylenedioxy-3α-hydroxy-6β-methyl-5α-pregnan-11-one (1.36 g) was dissolved in propan-2-ol (90 ml) and a solution of sodium borohydride (500 mg) in water (10 ml) was added. The solution was stirred at 20° overnight and then diluted with water (200 ml). Extraction with chloroform (2×100 ml) gave, on evaporation of the extract, a colourless gum which was dissolved in a mixture of acetone (50 ml) and 2N-hydrochloric acid (5 ml). After 2 hours the solution was diluted with water (100 ml) and extracted with chloroform (2×50 ml). Evaporation of the extract gave a colourless gum which was crystallised from methanol (25 ml) to give the title compound (700 mg), m.p. 211°-213°.

Workup

  1. extractionExtraction with chloroform (2×100 ml)
  2. customgave, on evaporation of the extract
  3. extractionextracted with chloroform (2×50 ml)
  4. customEvaporation of the extract
  5. customgave a colourless gum which
  6. customwas crystallised from methanol (25 ml)

Sources & evidence

ORD record
ord-1541cfdf95b8483ca7f8145c3b7d3384
Source dataset
uspto-grants-1980_03
Patent number
US04192871

Reaction notes

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