Ethanethiol → 21-Ethylthiomethyl-3alpha-hydroxy-5alpha-pregnane-11,20-dione

HRID 1973731Notes

Reaction equation

HRID 1973731 reaction equation
[OH:1][C@@H:2]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:19]2[C:18](=[O:24])[CH2:17][C@@:16]2([CH3:25])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:12](=[O:15])[CH:13]=[CH2:14])[CH2:3]1.[CH2:26]([SH:28])[CH3:27]>>[CH2:26]([S:28][CH2:14][CH2:13][C:12](=[O:15])[C@@H:11]1[C@:16]2([CH3:25])[C@H:8]([C@H:7]3[C@H:19]([C:18](=[O:24])[CH2:17]2)[C@:20]2([CH3:23])[C@H:4]([CH2:3][C@H:2]([OH:1])[CH2:22][CH2:21]2)[CH2:5][CH2:6]3)[CH2:9][CH2:10]1)[CH3:27]

Participants

3

Reactant 2

HCID 6343EthanethiolHCID 86734286HCID 86734286, compound

Product 1

HCID 8673430021-Ethylthiomethyl-3alpha-hydroxy-5alpha-pregnane-11,20-dione

Procedure

3α-Hydroxy-21-methylene-5α-pregnane-11,20-dione (250 mg. ) was dissolved in ethanethiol (2 ml) and the solution kept at room temperature for 24 hours. The excess ethanethiol was removed in vacuo and the residue partitioned between ether and water. The ethereal solution was washed with water, dried over anhydrous sodium sulphate and evaporated to a foam which was purified by preparative t.l.c. to give title compound (150 mg) as a glass [α]D + 83.3° (c = 0.12)

Workup

  1. customThe excess ethanethiol was removed in vacuo
  2. customthe residue partitioned between ether and water
  3. washThe ethereal solution was washed with water
  4. dry with materialdried over anhydrous sodium sulphate
  5. customevaporated to a foam which
  6. customwas purified by preparative t.l.c

Sources & evidence

ORD record
ord-6218cfacb41b459b8bf7acc843d47c0d
Source dataset
uspto-grants-1976_12
Patent number
US03998829

Reaction notes

Loading…