Water → HCID 131716313, compound

HRID 861645Notes

Reaction equation

HRID 861645 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]2[C@H:8]3[C@H:18]([CH2:19][CH2:20][C@:3]12[CH3:4])[C@:16]1([CH3:17])[C:11](=[CH:12][C:13](=[O:22])[CH2:14][C@@H:15]1[CH3:21])[CH2:10][CH2:9]3.[C:23]([O:26]C(=O)C)(=[O:25])[CH3:24].O>N1C=CC=CC=1>[C:23]([OH:26])(=[O:25])[CH3:24].[C:23]([OH:26])(=[O:25])[CH3:24].[OH:22][C:13]1[CH2:14][C@H:15]([CH3:21])[C@@:16]2([CH3:17])[C:11](=[CH:10][CH2:9][C@@H:8]3[C@@H:18]2[CH2:19][CH2:20][C@@:3]2([CH3:4])[C@H:5]3[CH2:6][CH2:7][C@@H:2]2[OH:1])[CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 10179417beta-Hydroxy-1alpha-methylandrost-4-ene-3-one

Product 1

HCID 131716313HCID 131716313, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

17β-Hydroxy-1α-methylandrost-4-en-3-one (1α-methyltestosterone, 1.0 g, 3.3 mmol) was dissolved in pyridine (10 ml) and acetic anhydride (10 ml) and stirred at room temperature under a drying tube for 18 hours. The mixture was poured into cold water and the precipitate collected and washed with additional cold water. After drying, the solid was chromatographed on flash SiO2 and eluted with 5% ether--95% hexane. There was obtained 1.18 g (93%) of 3,17β-dihydroxy-1α-methylandrosta-3,5-diene diactate 51, which was recrystallized from methanol-water: mp 111°-112° C.; NMR (CDCl3) δ 5.65 (d, J=3 Hz, 1H, H-4), 5.52 (br s, 1H, H-6), 4.64 (t, 1H, H-17), 2.10 (s, 3H, Ac), 2.02 (s, 3H, Ac), 1.05 (s, 3H, C-18 Me), 0.83 (s, 3H, C-19 Me), 0.86 (d, 3H, C-1 Me); IR (KBr) 2910, 1745, 1730, 1360, 1245, 1215; MS 386 (M+, 4), 358(1), 344(100), 329(2), 315 M* (344-329), 301(1), 151(1), 43(13); Anal. Calcd for C24H34 O4 : C, 74.57; H, 8.86. Found: C, 74-39; H, 8.62.

Workup

  1. customthe precipitate collected
  2. washwashed with additional cold water
  3. customAfter drying
  4. customthe solid was chromatographed on flash SiO2
  5. washeluted with 5% ether--95% hexane

Sources & evidence

ORD record
ord-ee3b1ac3740f4a56a9a1bdbdb5805610
Source dataset
uspto-grants-1998_02
Patent number
US05714481

Reaction notes

Loading…