Triethylamine → 11beta-Dipropylaminoacetoxy-3alpha-hydroxy-5alpha-pregnan-20-one

HRID 1701430Notes

Reaction equation

HRID 1701430 reaction equation
[CH2:1]([N:4]([CH2:8][C:9]([O:11][C@H:12]1[CH2:31][C@@:30]2([CH3:32])[C@@H:23]([CH2:24][CH2:25][C@@H:26]2[C:27](=[O:29])[CH3:28])[C@H:22]2[C@H:13]1[C@:14]1([CH3:34])[C@@H:19]([CH2:20][CH2:21]2)[CH2:18][C:17](=[O:33])[CH2:16][CH2:15]1)=[O:10])[CH2:5][CH2:6][CH3:7])[CH2:2][CH3:3].C(N(CC)CC)C>C(=O)(O)[O-].[Na+].O.Cl.Cl.Cl[Ir](Cl)(Cl)Cl>[CH2:1]([N:4]([CH2:8][C:9]([O:11][C@H:12]1[CH2:31][C@@:30]2([CH3:32])[C@@H:23]([CH2:24][CH2:25][C@@H:26]2[C:27](=[O:29])[CH3:28])[C@H:22]2[C@H:13]1[C@:14]1([CH3:34])[C@@H:19]([CH2:20][CH2:21]2)[CH2:18][C@H:17]([OH:33])[CH2:16][CH2:15]1)=[O:10])[CH2:5][CH2:6][CH3:7])[CH2:2][CH3:3]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 7058369811beta-Dipropylaminoacetoxy-5alpha-pregnane-3,20-dione

Product 1

HCID 2281032311beta-Dipropylaminoacetoxy-3alpha-hydroxy-5alpha-pregnan-20-one

Reagents, catalysts & solvents 2

HCID 16211483Tetrachloroiridium--hydrogen chloride--water (1/2/1)CatalystHCID 516892Sodium BicarbonateSolvent

Procedure

11β-Dipropylaminoacetoxy-5α-pregnane-3,20-dione (300 mg) was added to a solution of chloroiridic acid reagent (10 ml) containing triethylamine (1.1 ml). The mixture was boiled for about 20 minutes, cooled and diluted with sodium bicarbonate solution and the precipitated solid collected by filtration to afford title compound, m.p. 107°-115°, [α]D +91.3° (230 mg).

Workup

  1. temperaturecooled
  2. filtrationthe precipitated solid collected by filtration

Sources & evidence

ORD record
ord-b6694a3c81e8453abc5839ffbb513d5d
Source dataset
uspto-grants-1980_03
Patent number
US04192871

Reaction notes

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