Water → HCID 131719766, compound

HRID 232765Notes

Reaction equation

HRID 232765 reaction equation
C(N(CC)CC)C.[OH:8][CH:9]1[CH2:14][CH2:13][N:12]([C@H:15]2[CH2:32][C@@:31]3([CH3:33])[C@@H:18]([CH2:19][CH2:20][C@@H:21]4[C@@H:30]3[CH2:29][CH2:28][C@@:26]3([CH3:27])[C@H:22]4[CH2:23][C@H:24]([N:35]4[CH2:39][CH2:38][CH2:37][CH2:36]4)[C@@H:25]3[OH:34])[CH2:17][C@@H:16]2[OH:40])[CH2:11][CH2:10]1.[C:41](Cl)(=[O:43])[CH3:42].[OH2:45]>C(Cl)Cl>[C:41]([O:8][CH:9]1[CH2:14][CH2:13][N:12]([C@H:15]2[CH2:32][C@@:31]3([CH3:33])[C@@H:18]([CH2:19][CH2:20][C@@H:21]4[C@@H:30]3[CH2:29][CH2:28][C@@:26]3([CH3:27])[C@H:22]4[CH2:23][C@H:24]([N:35]4[CH2:39][CH2:38][CH2:37][CH2:36]4)[C@@H:25]3[OH:34])[CH2:17][C@@H:16]2[OH:40])[CH2:11][CH2:10]1)(=[O:43])[CH3:42].[CH3:42][C:41]([CH2:26][C:25]([OH:34])=[O:45])=[O:43]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chloride2×HCID 8471TriethylamineHCID 676844432beta-(4-Hydroxy-1-piperidinyl)-16beta-(1-pyrrolidinyl)-5alpha-androstane-3alpha,17beta-diol

Product 1

HCID 131719766HCID 131719766, compoundYield 71.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

After adding 7.9 g of triethylamine to a solution containing 9 g of 2β-(4-hydroxy-1-piperidinyl)-16β-(1-pyrrolidinyl)-5α-androstane-3α,17β-diol in 80 ml of methylene chloride, 9 g of acetyl chloride are dropwise added to the solution at a temperature of 0° C. under cooling and stirring. After termination of the addition, the reaction mixture is maintained at room temperature for 24 hours. After completion of the reaction the excess of acetyl chloride is decomposed by water, the methylene chloride solution is washed with aqueous sodium hydroxide solution until it becomes acid-free, then washed with water several times until neutral. After drying the methylene chloride solution and evaporating, the residue is purified on a silica gel column to yield 8.3 g (71.9%) of the title compound, Rf1 =0.36.

Workup

  1. additionare dropwise added to the solution at a temperature of 0° C.
  2. temperatureunder cooling
  3. additionAfter termination of the addition
  4. washthe methylene chloride solution is washed with aqueous sodium hydroxide solution until it
  5. washwashed with water several times until neutral
  6. dry with materialAfter drying the methylene chloride solution
  7. customevaporating
  8. customthe residue is purified on a silica gel column

Sources & evidence

ORD record
ord-814c7bc39f994a15a7276232e38c89aa
Source dataset
uspto-grants-1997_01
Patent number
US05591735

Reaction notes

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