Benzyl mercaptan → 21-Benzylthio-3alpha-hydroxy-5alpha-pregnane-11,20-dione

HRID 1077009Notes

Reaction equation

HRID 1077009 reaction equation
[C:1]1([CH2:7][SH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na].Br[CH2:11][C:12](=[O:34])[C@@H:13]1[C@:30]2([CH3:31])[C@H:16]([C@H:17]3[C@H:27]([C:28](=[O:32])[CH2:29]2)[C@:25]2([CH3:26])[C@H:20]([CH2:21][C@H:22]([OH:33])[CH2:23][CH2:24]2)[CH2:19][CH2:18]3)[CH2:15][CH2:14]1>CC(O)C.C1(C)C=CC=CC=1>[CH2:7]([S:8][CH2:11][C:12](=[O:34])[C@@H:13]1[C@:30]2([CH3:31])[C@H:16]([C@H:17]3[C@H:27]([C:28](=[O:32])[CH2:29]2)[C@:25]2([CH3:26])[C@H:20]([CH2:21][C@H:22]([OH:33])[CH2:23][CH2:24]2)[CH2:19][CH2:18]3)[CH2:15][CH2:14]1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 7509Benzyl mercaptanHCID 5360545SodiumHCID 8673346721-Bromo-3alpha-hydroxy-5alpha-pregnane-11,20-dione

Product 1

HCID 8673346821-Benzylthio-3alpha-hydroxy-5alpha-pregnane-11,20-dione

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3776IsopropanolSolvent

Procedure

Toluene-α-thiol (1.0 ml.) was added to a warm solution of sodium (0.6 g.) in a mixture of propan-2-ol (25 ml.) and toluene (30 ml.). 21-Bromo-3α-hydroxy-5α-pregnane-11,20 -dione (0.7 g.) was then added and the mixture was gently refluxed for 2 hr. The mixture was then partitioned between water and ether and the organic layer was washed with water, dried (Na2SO4) and evaporated. The residue was purified by preparative t.l.c. (CHCl3) to give title compound (0.4 g.) as a white foam, [α]D + 89° (c 1.1).

Workup

  1. temperaturethe mixture was gently refluxed for 2 hr
  2. customThe mixture was then partitioned between water and ether
  3. washthe organic layer was washed with water
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe residue was purified by preparative t.l.c

Sources & evidence

ORD record
ord-be45fe49846a4b849ed0a10e61235ffb
Source dataset
uspto-grants-1976_05
Patent number
US03959260

Reaction notes

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