Isopropanol → HCID 22788259, compound

HRID 267625Notes

Reaction equation

HRID 267625 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][O:9][C:10]([C@H:12]2[CH2:17][CH2:16][C@H:15]3[C@H:18]4[C@H:28]([CH2:29][CH2:30][C@:13]23[CH3:14])[C@:26]2([CH3:27])[C@H:21]([CH2:22][C:23](=[O:31])[CH2:24][CH2:25]2)[CH2:20][CH2:19]4)=[O:11])[CH2:3][CH2:2]1.C(O)(C)C.C(N(CC)CC)C>O>[OH:31][C@@H:23]1[CH2:24][CH2:25][C@@:26]2([CH3:27])[C@@H:21]([CH2:20][CH2:19][C@@H:18]3[C@@H:28]2[CH2:29][CH2:30][C@@:13]2([CH3:14])[C@H:15]3[CH2:16][CH2:17][C@@H:12]2[C:10]([O:9][CH2:8][CH2:7][N:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)=[O:11])[CH2:22]1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 8471TriethylamineHCID 22788248HCID 22788248, compound

Product 1

HCID 22788259HCID 22788259, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 17β(2'-morpholinoethoxycarbonyl)-5α-androstan-3-one (750 mg.) in the minimum volume of isopropanol was added to a stock solution (35 ml.) of chloroiridic acid/trimethyl phosphite complex preneutralised to pH5 with triethylamine (3 ml.). This solution, after being refluxed for 4.5 hours, was poured into water and extracted with chloroform. The chloroform solution was washed with water, dried (MgSO4) and filtered through a short column of florisil before evaporation to a gum (740 mg.). Purification by preparative t.l.c. (ethanol/chloroform 1:19) afforded title compound (545 mg.) as a white froth; [α]D + 37.8, (c 0.9%).

Workup

  1. temperatureThis solution, after being refluxed for 4.5 hours
  2. extractionextracted with chloroform
  3. washThe chloroform solution was washed with water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered through a short column of florisil before evaporation to a gum (740 mg.)
  6. customPurification by preparative t.l.c

Sources & evidence

ORD record
ord-f455ff8ae7ae4dc6a5de8233a4c1c771
Source dataset
uspto-grants-1976_03
Patent number
US03943124

Reaction notes

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