Water → HCID 86584404, compound

HRID 2227243Notes

Reaction equation

HRID 2227243 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:16]([O:19][C@H:20]1[CH2:25][CH2:24][C@H:23]2[C@H:26]3[C@H:35]([CH2:36][CH2:37][C@:21]12[CH3:22])[C@@H:34]1[C:29]([CH2:30][C@@H:31]([OH:38])[CH2:32][CH2:33]1)=[CH:28][CH2:27]3)(=[O:18])[CH3:17].O>CN(C)C1C=CN=CC=1.CN(C=O)C>[C:16]([O:19][C@H:20]1[CH2:25][CH2:24][C@H:23]2[C@H:26]3[C@H:35]([CH2:36][CH2:37][C@:21]12[CH3:22])[C@@H:34]1[C:29]([CH2:30][C@@H:31]([O:38][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH2:32][CH2:33]1)=[CH:28][CH2:27]3)(=[O:18])[CH3:17]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 69828917HCID 69828917, compound

Product 1

HCID 86584404HCID 86584404, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

Prepare O93 from O92 by treating with acetic anhydride as described for the synthesis of J62 in example 10a, and then treat O93 with sodium borohydride to provide O94 as described for the preparation of J63 in example 10b. Add t-butyldimethylsilyl chloride (16.44 g, 109.1 mmol), 4-dimethylaminopyridine (0.62 g, 5.20 mmol) and triethylamine (15.9 mL, 114.3 mmol) to a stirred solution of estr-5-ene-3β,17β-diol 17-acetate (O94, 33.1 g, 103.9 mmol, Campbell, J. A. and Babcock, J. C., 1971, U.S. Pat. No. 3,597,418) in anhydrous DMF (350 mL) under nitrogen. Stir the resultant suspension at room temperature for 3 days and then pour into vigorously stirred water (2.5 L). Filter the resultant suspension to give 3β-[[(1,1-dimethylethyl)dimethylsilyl]oxy]estr-5-en-17β-ol 17 acetate (O95) as an off-white solid.

Workup

  1. customas described for the preparation of J63 in example 10b
  2. filtrationFilter the resultant suspension

Sources & evidence

ORD record
ord-0d91a8e44b454857910cd59feca33af1
Source dataset
uspto-grants-2002_07
Patent number
US06413951B2

Reaction notes

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