Water → HCID 22795163, compound

HRID 1973737Notes

Reaction equation

HRID 1973737 reaction equation
Cl[CH2:2][CH2:3][C:4](=[O:26])[C@@H:5]1[C@:22]2([CH3:23])[C@H:8]([C@H:9]3[C@H:19]([C:20](=[O:24])[CH2:21]2)[C@:17]2([CH3:18])[C@H:12]([CH2:13][C@H:14]([OH:25])[CH2:15][CH2:16]2)[CH2:11][CH2:10]3)[CH2:7][CH2:6]1.[C:27]1(=[O:37])[NH:31][C:30](=[O:32])[C:29]2=[CH:33][CH:34]=[CH:35][CH:36]=[C:28]12.[K].O>CC(C)=O>[OH:25][C@@H:14]1[CH2:15][CH2:16][C@@:17]2([CH3:18])[C@@H:12]([CH2:11][CH2:10][C@@H:9]3[C@@H:19]2[C:20](=[O:24])[CH2:21][C@@:22]2([CH3:23])[C@H:8]3[CH2:7][CH2:6][C@@H:5]2[C:4](=[O:26])[CH2:3][CH2:2][N:31]2[C:27](=[O:37])[C:28]3=[CH:36][CH:35]=[CH:34][CH:33]=[C:29]3[C:30]2=[O:32])[CH2:13]1

Participants

5

Reactant 3

HCID 962WaterHCID 24194345Phthalimide potassium saltHCID 8673430721-Chloromethyl-3alpha-hydroxy-5alpha-pregnane-11,20-dione

Product 1

HCID 22795163HCID 22795163, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

21-Chloromethyl-3α-hydroxy-5α-pregnane-11,20-dione (600 mg) in acetone was treated at reflux with potassium phthalimide (600 mg) for 10 hours, poured into water and the oily precipitate extracted into ether. The extracts were washed with water, dried over anhydrous sodium sulphate and evaporated to a white foam (700 mg). Purification by preparative t.l.c. in ethyl acetate/petrol (1:1) gave a foam which on trituration with ether gave title compound (490 mg) as a white solid m.p. 187°-189° [α]D + 58.8° (c = 0.97).

Workup

  1. extractionthe oily precipitate extracted into ether
  2. washThe extracts were washed with water
  3. dry with materialdried over anhydrous sodium sulphate
  4. customevaporated to a white foam (700 mg)
  5. customPurification by preparative t.l.c
  6. customin ethyl acetate/petrol (1:1) gave a foam which on trituration with ether

Sources & evidence

ORD record
ord-ce8a375cde5e4420abea5eb96e3232ff
Source dataset
uspto-grants-1976_12
Patent number
US03998829

Reaction notes

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