Bromine → HCID 131710459, compound

HRID 1576791Notes

Reaction equation

HRID 1576791 reaction equation
[OH:1][C@@H:2]1[C@@H:21]([CH3:22])[CH2:20][C@@:19]2([CH3:23])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:18]2[C:17](=[O:24])[CH2:16][C@@:15]2([CH3:25])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:12](=[O:14])[CH3:13])[CH2:3]1.[Br:26]Br>CO>[Br:26][CH2:13][C:12](=[O:14])[C@@H:11]1[C@:15]2([CH3:25])[C@H:8]([C@H:7]3[C@H:18]([C:17](=[O:24])[CH2:16]2)[C@:19]2([CH3:23])[C@H:4]([CH2:3][C@H:2]([OH:1])[C@@H:21]([CH3:22])[CH2:20]2)[CH2:5][CH2:6]3)[CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 24408BromineHCID 86733283HCID 86733283, compound

Product 1

HCID 131710459HCID 131710459, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 3α-hydroxy-2β-methyl-5α-pregnane-11,20-dione (1.04g.) in dry methanol (150ml) was stirred at 0°-5° during the dropwise addition of a solution of bromine (0.16ml) in dry methanol (20ml) over a period of 2.5 hours. The reaction mixture was partitioned between ethyl acetate and water and the organic layer was separated, washed with water, dried (MgSO4) and evaporated to a white foam; purification by preparative t.l.c. (ethyl acetate: benzene 1:2.5) gave the title compound (510mg.), m.p. 140° dec.; [α]D + 133° (c 0.95).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. customthe organic layer was separated
  3. washwashed with water
  4. dry with materialdried (MgSO4)
  5. customevaporated to a white foam
  6. custompurification by preparative t.l.c

Sources & evidence

ORD record
ord-3b3bea7058c44df4a69d3924b0431d53
Source dataset
uspto-grants-1976_09
Patent number
US03983111

Reaction notes

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