Chlorotrimethylsilane → HCID 22866440, compound

HRID 1585513Notes

Reaction equation

HRID 1585513 reaction equation
[CH3:1][Si:2](Cl)([CH3:4])[CH3:3].[OH:6][C@H:7]1[CH2:33][CH2:32][C@@:31]2([CH3:34])[C@@H:9]([CH2:10][CH2:11][C@@H:12]3[C@@H:30]2[C:29](=[O:35])[CH2:28][C@@:27]2([CH3:36])[C@H:13]3[CH2:14][C@@H:15]3[O:20][C@@:19]4([O:26][CH2:25][C@H:23]([CH3:24])[CH2:22][CH2:21]4)[C@@H:17]([CH3:18])[C@@H:16]32)[CH2:8]1.C(N(CC)CC)C.CC1C=CN=C(N)C=1C>ClCCl>[CH3:1][Si:2]([CH3:4])([CH3:3])[O:6][C@H:7]1[CH2:33][CH2:32][C@@:31]2([CH3:34])[C@@H:9]([CH2:10][CH2:11][C@@H:12]3[C@@H:30]2[C:29](=[O:35])[CH2:28][C@@:27]2([CH3:36])[C@H:13]3[CH2:14][C@@H:15]3[O:20][C@@:19]4([O:26][CH2:25][C@H:23]([CH3:24])[CH2:22][CH2:21]4)[C@@H:17]([CH3:18])[C@@H:16]32)[CH2:8]1

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 736823-Hydroxyspirostan-11-oneHCID 110078842-Amino-3,4-dimethylpyridine

Product 1

HCID 22866440HCID 22866440, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trimethylsilylchloride (3.27 mL, 25.8 mmol) was added to a solution of (3β,5α,25R)3-hydroxy-spirostan-11-one (4.0 g, 9.3 mmol) and triethylamine (6.5 mL, 46 mmol) in dichloromethane (60 mL) at room temperature. One gram of dimethyl aminopyridine was added and the reaction was stirred at room temperature for 12 hours. The reaction was quenched with methanol (1 mL) and diluted with ethyl acetate, washed with water (5×) and brine (1×), dried (Na2SO4), filtered and concentrated in vacuo. The product was triturated with methanol, filtered and dried to afford 3.94 g (85%) product as a white solid. 1H NMR (250 MHz, CDCl3) 6 4.5 (q, 1H, J=6Hz); 3.45 (m, 2H); 2.35 (t, 1H, J=10 Hz); 2.4 (dt, 1H, J=12.2 Hz); 2.2 (s, 2H); 2.1-1.1 (m, 12H); 1.02 (s, 3H); 0.9 (d, 3H, J=7.0 Hz); 0.78 (d, 3H, J=7 Hz); 0.69 (s, 3H); 0.1 (s, 9H).

Workup

  1. customThe reaction was quenched with methanol (1 mL)
  2. additiondiluted with ethyl acetate
  3. washwashed with water (5×) and brine (1×)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe product was triturated with methanol
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-36bb5a9dca834f679f393e0bba651ff9
Source dataset
uspto-grants-1999_08
Patent number
US05939398

Reaction notes

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