Hydrochloric Acid → 15,15-Dimethylestra-1,3,5(10)-triene-3,17beta-diol

HRID 2256870Notes

Reaction equation

[H-].C([Al+]CC(C)C)C(C)C.C[O:12][C:13]1[CH:30]=[CH:29][C:28]2[C@@H:27]3[C@H:18]([C@H:19]4[C@@:23]([CH2:25][CH2:26]3)([CH3:24])[C@@H:22]([OH:31])[CH2:21][C:20]4([CH3:33])[CH3:32])[CH2:17][CH2:16][C:15]=2[CH:14]=1.[Cl-].[NH4+].Cl>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:32][C:20]1([CH3:33])[C@H:19]2[C@H:18]3[C@H:27]([CH2:26][CH2:25][C@:23]2([CH3:24])[C@@H:22]([OH:31])[CH2:21]1)[C:28]1[CH:29]=[CH:30][C:13]([OH:12])=[CH:14][C:15]=1[CH2:16][CH2:17]3

Participants

Conditions

Temperature: 0 °C

Procedure

Representative Procedure: Diisobutylaluminum hydride (0.5 ml; 1.5M; 0.75 mmol) was added to a solution of the 5,15-dimethyl-17β-alcohol (12) in dry toluene (5 ml). The solution was heated to refluxing temperature for 24 h. The mixture was cooled to 0° C., saturated aqueous ammonium chloride was added, and the aqueous phase was further acidified with dilute HCl. The standard work-up (ethyl acetate) gave 15,15-dimethylestra-1,3,5(10)-triene-3,17β-diol (16) (43 mg; 90%), m.p. 167-170 (from ethyl acetate); [α]D +49° (c 1.1 ethanol) (Found; C, 79.6; H, 9.3%; M+, 300. C20H28O2 requires C, 80.0; H, 9.4%; M, 300).

Workup

temperatureThe solution was heated
temperatureto refluxing temperature for 24 h

Sources & evidence

ORD record: ord-3abf6b3864b24c6a932082ee641c6b16
Source dataset: uspto-grants-1997_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05656622

Reaction notes

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