Triethylamine → 3-(tert-Butyldimethylsiloxy)androsta-3,5-diene-11,17-dione

HRID 53187Notes

Reaction equation

HRID 53187 reaction equation
[CH3:1][C@@:2]12[C@H:12]3[C:13]([CH2:15][C@:16]4([CH3:22])[C:20](=[O:21])[CH2:19][CH2:18][C@H:17]4[C@@H:11]3[CH2:10][CH2:9][C:8]1=[CH:7][C:5](=[O:6])[CH2:4][CH2:3]2)=[O:14].C(N(CC)CC)C.FC(F)(F)S(O[Si:36]([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:38])[CH3:37])(=O)=O>ClCCl>[O:6]([C:5]1[CH2:4][CH2:3][C@@:2]2([CH3:1])[C:8](=[CH:9][CH2:10][C@@H:11]3[C@@H:12]2[C:13](=[O:14])[CH2:15][C@@:16]2([CH3:22])[C@H:17]3[CH2:18][CH2:19][C:20]2=[O:21])[CH:7]=1)[Si:36]([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:38])[CH3:37]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 223997Adrenosterone

Product 1

HCID 228699373-(tert-Butyldimethylsiloxy)androsta-3,5-diene-11,17-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of adrenosterone (6.0 g, 20 mmol) in dry, dichloromethane (120 ml) was added triethylamine (8.4 ml, 60 mmol) followed by tert-butyldimethylsilyl trifluoromethanesulfonate (5.0 ml, 22 mmol) and the mixture stirred at room temperature for 3 h. The dichloromethane was evaporated and the residue redissolved in diethyl ether (100 ml), then allowed to stand for 30 min, after which time an oil separated. The ether phase was decanted off the oil and the solvent evaporated to give the title compound which was used directly in step (b). IR νmax 1705, 1747 cm-1 ; 1H-NMR(CDCl3) inter alia δ0.12 (6H,s,Me2Si), 0.85 (3H,s,18-CH3), 0.92 (9H,s,tBuSi) 1.17(3H,s, 19-CH3), 4.73 (1H,dm, J 6.9Hz, 6-H), 5.36 (1H,m,4-H).

Workup

  1. customThe dichloromethane was evaporated
  2. dissolutionthe residue redissolved in diethyl ether (100 ml)
  3. waitto stand for 30 min
  4. customafter which time an oil separated
  5. customThe ether phase was decanted off the oil
  6. customthe solvent evaporated

Sources & evidence

ORD record
ord-f92ef8dd33944c519cb45687070ba923
Source dataset
uspto-grants-1997_04
Patent number
US05618807

Reaction notes

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