Sodium borohydride → HCID 54222593, compound

HRID 866517Notes

Reaction equation

HRID 866517 reaction equation
[CH2:1]1[C@H:3]2[C:4](=[O:22])[CH:5]=[C:6]3[C@:19]([CH3:20])([C@@H:2]12)[C@@H:18]1[C@H:9]([C@H:10]2[C@@:14]([CH2:16][CH2:17]1)([CH3:15])[C:13](=[O:21])[CH2:12][CH2:11]2)[CH2:8][CH2:7]3.[BH4-].[Na+].P([O-])(O)(O)=O.[Na+]>C(O)C>[OH:21][C@H:13]1[CH2:12][CH2:11][C@H:10]2[C@H:9]3[C@H:18]([CH2:17][CH2:16][C@:14]12[CH3:15])[C@:19]1([CH3:20])[C:6](=[CH:5][C:4](=[O:22])[C@@H:3]2[CH2:1][C@@H:2]21)[CH2:7][CH2:8]3

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 23672064Monosodium phosphateHCID 54262379HCID 54262379, compound

Product 1

HCID 54222593HCID 54222593, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3.2 g. of 1α,2α-methylene-4-androstene-3,17-dione is dissolved in 50 ml. of absolute ethanol, cooled to 0° C., and mixed with 0.5 g. of sodium borohydride in incremental portions. After a reaction period of 3 hours with ice cooling. The mixture is stirred into 50 ml. of semisaturated sodium dihydrogen phosphate solution. The thus-precipitated product is filtered off and washed with water. After recrystallization from ethanol, 1.95 g. of 17β-hydroxy-1α,2α-methylene-4-androsten-3-one is obtained and gives after acetylation with acetic anhydridepyridine at room temperature, strongly anabolic 17β-acetoxy-1α,2α-methylene-4,6-androsten-3-one, "Arzneim. Forschung" (Drug Research) 15 (1965) : 1168.

Workup

  1. additionmixed with 0.5 g
  2. customAfter a reaction period of 3 hours with ice cooling
  3. filtrationThe thus-precipitated product is filtered off
  4. washwashed with water
  5. customAfter recrystallization from ethanol, 1.95 g

Sources & evidence

ORD record
ord-72caddedbd954052bbadae641d0d71be
Source dataset
uspto-grants-1978_07
Patent number
US04100026

Reaction notes

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