Water → HCID 131719773, compound

HRID 232778Notes

Reaction equation

HRID 232778 reaction equation
C(N([CH2:6][CH3:7])CC)C.[C:8](Cl)(=[O:10])[CH3:9].[OH:12][CH:13]1[CH2:18][CH2:17][N:16]([C@H:19]2[CH2:36][C@@:35]3([CH3:37])[C@@H:22]([CH2:23][CH2:24][C@@H:25]4[C@@H:34]3[CH2:33][CH2:32][C@@:30]3([CH3:31])[C@H:26]4[CH2:27][C@H:28]([N:39]4[CH2:44][CH2:43][CH:42]([OH:45])[CH2:41][CH2:40]4)[C@@H:29]3[OH:38])[CH2:21][C@@H:20]2[OH:46])[CH2:15][CH2:14]1.[OH2:47]>C(Cl)Cl>[C:8]([O:12][CH:13]1[CH2:18][CH2:17][N:16]([C@H:19]2[CH2:36][C@@:35]3([CH3:37])[C@@H:22]([CH2:23][CH2:24][C@@H:25]4[C@@H:34]3[CH2:33][CH2:32][C@@:30]3([CH3:31])[C@H:26]4[CH2:27][C@H:28]([N:39]4[CH2:44][CH2:43][CH:42]([O:45][C:6](=[O:47])[CH3:7])[CH2:41][CH2:40]4)[C@@H:29]3[OH:38])[CH2:21][C@@H:20]2[OH:46])[CH2:15][CH2:14]1)(=[O:10])[CH3:9].[CH3:9][C:8]([CH2:43][C:42]([OH:45])=[O:47])=[O:10]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chloride2×HCID 8471TriethylamineHCID 67684266HCID 67684266, compound

Product 1

HCID 131719773HCID 131719773, compoundYield 74.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

After adding 21 ml of triethylamine and then 17 ml of acetyl chloride to 15.0 g of 2β,16β-bis(4-hydroxy-1-piperidinyl)-5α-androstane-3α,17β-diol dissolved in 85 ml of methylene chloride, the solution is left to stand for 12 hours, then the excess of acetyl chloride is decomposed by water. The methylene chloride solution is washed first with an aqueous sodium hydroxide solution cooled to 2°-5° C. and then with water until it becomes neutral. After drying, methylene chloride is evaporated to obtain the title compound as a foam-like residue in a yield of 74.9%, Rf3 =0.67.

Workup

  1. waitthe solution is left
  2. washThe methylene chloride solution is washed first with an aqueous sodium hydroxide solution
  3. temperaturecooled to 2°-5° C.
  4. customAfter drying
  5. custommethylene chloride is evaporated

Sources & evidence

ORD record
ord-ff034d13edf64cc79bf3085cf4ee84f0
Source dataset
uspto-grants-1997_01
Patent number
US05591735

Reaction notes

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