Acetyl chloride → Androstan-17-one, 3-(acetyloxy)-2,16-di-1-piperidinyl-, (2β,3α,5α,16β)-

HRID 36841Notes

Reaction equation

HRID 36841 reaction equation
[OH:1][C@@H:2]1[C@@H:19]([N:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[CH2:18][C@@:17]2([CH3:26])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:16]2[CH2:15][CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][C@H:10]([N:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)[C:11]2=[O:27])[CH2:3]1.[C:34](Cl)(=[O:36])[CH3:35]>ClCCl>[C:34]([O:1][C@@H:2]1[C@@H:19]([N:20]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]2)[CH2:18][C@@:17]2([CH3:26])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:16]2[CH2:15][CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][C@H:10]([N:28]3[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]3)[C:11]2=[O:27])[CH2:3]1)(=[O:36])[CH3:35]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 1146563beta-Hydroxy-2beta,16beta-dipiperidino-5-alpha-androstan-17-one

Product 1

HCID 22853572Androstan-17-one, 3-(acetyloxy)-2,16-di-1-piperidinyl-, (2β,3α,5α,16β)-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 40 g of (2β,3α,5α,16β)-3-hydroxy-2,16-di-(1-piperidinyl)-androstan-17-one in 160 ml of dichloromethane were added 13.5 ml of acetylchloride at 15°-20 ° C. The solution was stirred for 6 h at room temperature and thereafter evaporated to dryness. The residue was dissolved in toluene, the solution again evaporated to dryness and the residue dissolved in dichloromethane. The solution was washed with saturated aqueous sodium carbonate solution, with water and with saturated brine, dried over sodium sulphate, and evaporated to dryness to give 43.5 g of (2β,3α,5α,16β)-3-acetyloxy-2,16-di-(1-piperidinyl)androstan-17-one. Mp 154° C.

Workup

  1. customevaporated to dryness
  2. dissolutionThe residue was dissolved in toluene
  3. customthe solution again evaporated to dryness
  4. dissolutionthe residue dissolved in dichloromethane
  5. washThe solution was washed with saturated aqueous sodium carbonate solution, with water and with saturated brine
  6. dry with materialdried over sodium sulphate
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-bd8175091f0e4c5691795727be49dd1c
Source dataset
uspto-grants-1995_05
Patent number
US05418226

Reaction notes

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