Triethylamine → 3alpha-Hydroxy-17beta(3'-morpholinopropoxycarbonyl)-5alpha-androstan-11-one

HRID 267624Notes

Reaction equation

HRID 267624 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][CH2:9][O:10][C:11]([C@H:13]2[CH2:18][CH2:17][C@H:16]3[C@H:19]4[C@H:29]([C:30](=[O:32])[CH2:31][C@:14]23[CH3:15])[C@:27]2([CH3:28])[C@H:22]([CH2:23][C:24](=[O:33])[CH2:25][CH2:26]2)[CH2:21][CH2:20]4)=[O:12])[CH2:3][CH2:2]1.C(N(CC)CC)C>C(O)(C)C.O.Cl.Cl.Cl[Ir](Cl)(Cl)Cl>[OH:33][C@@H:24]1[CH2:25][CH2:26][C@@:27]2([CH3:28])[C@@H:22]([CH2:21][CH2:20][C@@H:19]3[C@@H:29]2[C:30](=[O:32])[CH2:31][C@@:14]2([CH3:15])[C@H:16]3[CH2:17][CH2:18][C@@H:13]2[C:11]([O:10][CH2:9][CH2:8][CH2:7][N:4]2[CH2:3][CH2:2][O:1][CH2:6][CH2:5]2)=[O:12])[CH2:23]1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 2278824917beta(3'-Morpholinopropoxycarbonyl)-5alpha-androstan-3,11-dione

Product 1

HCID 227882623alpha-Hydroxy-17beta(3'-morpholinopropoxycarbonyl)-5alpha-androstan-11-one

Reagents, catalysts & solvents 2

HCID 16211483Tetrachloroiridium--hydrogen chloride--water (1/2/1)CatalystHCID 3776IsopropanolSolvent

Procedure

A solution of 17β(3'-morpholinopropoxycarbonyl)-5α-androstan-3,11-dione (140 mg.) in isopropanol (1 ml.) was added to a "stock" solution of the chloroiridic acid reagent (7 ml.) which had been neutralised to ca. pH 6 with triethylamine immediately prior to the addition. After refluxing for 7 hr., isolation of the product afforded a gum (150 mg.) which, after purification by preparative t.l.c., gave the title compound as a white froth; 112 mg., [α]D + 51° (c, 0.6,).

Workup

  1. additionto the addition
  2. temperatureAfter refluxing for 7 hr
  3. custom, isolation of the product afforded a gum (150 mg.) which
  4. customafter purification by preparative t.l.c

Sources & evidence

ORD record
ord-0d978c6325eb4f3c824f618eb42154a7
Source dataset
uspto-grants-1976_03
Patent number
US03943124

Reaction notes

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