Water → HCID 10993121, compound

HRID 2227238Notes

Reaction equation

HRID 2227238 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:16][C@@:17]12[C:25](=[O:26])[CH2:24][CH2:23][C@H:22]1[C@@H:21]1[CH2:27][CH:28]=[C:29]3[CH2:34][C@@H:33]([OH:35])[CH2:32][CH2:31][C@:30]3([CH3:36])[C@H:20]1[CH2:19][CH2:18]2.O>CN(C)C1C=CN=CC=1.CN(C=O)C>[CH3:5][C:4]([Si:1]([CH3:3])([CH3:2])[O:35][C@H:33]1[CH2:32][CH2:31][C@@:30]2([CH3:36])[C:29](=[CH:28][CH2:27][C@@H:21]3[C@@H:20]2[CH2:19][CH2:18][C@@:17]2([CH3:16])[C@H:22]3[CH2:23][CH2:24][C:25]2=[O:26])[CH2:34]1)([CH3:7])[CH3:6]

Participants

7

Reactant 4

HCID 962WaterHCID 5881DehydroepiandrosteroneHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 10993121HCID 10993121, compoundYield 88.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

Add t-butyldimethylsilyl chloride (10.97 g, 72.8 mmol), 4-dimethylaminopyridine (0.42 g, 3.47 mmol) and triethylamine (10.63 mL, 76.27 mmol) to a stirred solution of dehydroepiandrosterone (A1, 20.00 g, 69.3 mmol) in anhydrous DMF (350 mL) under nitrogen. Stir the resultant suspension at room temperature for 3 days and then pour into rapidly stirred water (1.5 L). Filter the resultant suspension and recrystallize the white solid from aqueous acetone to give A2 (24.64 g, 88%) as a white crystalline solid: mp 146-148° C. TLC Rf 0.78, ethyl acetate/hexane (1:1); 1H NMR δ 5.38-5.32 (m, 1H), 3.55-3.43 (m, 1H), 1.03 (s, 3H), 0.89 (s, 9H), 0.88(s, 3H), 0.06 (s, 6H); MS (CI, CH4) m/z (rel intensity) 403 (MH+, 3), 401 (5), 387 (9), 345 (18), 271 (100). Analysis Calculated for C25H42SiO2: C, 74.57; H, 10.51. Found: C, 74.89; H, 10.84.

Workup

  1. filtrationFilter the resultant suspension
  2. customrecrystallize the white solid from aqueous acetone

Sources & evidence

ORD record
ord-496283529ab843f2996698bd97769594
Source dataset
uspto-grants-2002_07
Patent number
US06413951B2

Reaction notes

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