Water → HCID 12149919, compound

HRID 2227241Notes

Reaction equation

HRID 2227241 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[OH:9][C@H:10]1[CH2:27][CH2:26][C@@:25]2([CH3:28])[C:12](=[CH:13][CH2:14][C@@H:15]3[C@@H:24]2[CH2:23][CH2:22][C@@:20]2([CH3:21])[C@H:16]3[CH:17]=[CH:18][C:19]2=[O:29])[CH2:11]1.O>CN(C)C1C=CN=CC=1.CN(C=O)C>[CH3:5][C:4]([Si:1]([CH3:3])([CH3:2])[O:9][C@H:10]1[CH2:27][CH2:26][C@@:25]2([CH3:28])[C:12](=[CH:13][CH2:14][C@@H:15]3[C@@H:24]2[CH2:23][CH2:22][C@@:20]2([CH3:21])[C@H:16]3[CH:17]=[CH:18][C:19]2=[O:29])[CH2:11]1)([CH3:7])[CH3:6]

Participants

6

Reactant 3

HCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 110552793beta-hydroxyandrosta-5,15-dien-17-one

Product 1

HCID 12149919HCID 12149919, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

Add t-butyldimethylsilyl chloride (5.49 g, 36.4 mmol), 4-dimethylaminopyridine (0.21 g, 1.74 mmol) and triethylarmine (5.32 mL, 38.14 mmol) to a stirred solution of 3β-hydroxyandrosta-5,15-dien-17-one (M81, 10.00 g, 34.8 mmol) in anhydrous DMF (175 mL) under nitrogen. Stir the resultant suspension at room temperature for 3 days and then pour into rapidly stirred water (750 mL). Filter the resultant suspension and crystallize the white solid to give 3β-[[(1,1-dimethylethyl)dimethylsilyl]oxy]androst-5,15-dien-17-one (M82).

Workup

  1. filtrationFilter the resultant suspension
  2. customcrystallize the white solid

Sources & evidence

ORD record
ord-baf32760557240fe89c3d41f6bb4c4b1
Source dataset
uspto-grants-2002_07
Patent number
US06413951B2

Reaction notes

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