Water → HCID 67855816, compound

HRID 1613978Notes

Reaction equation

[H-].C([Al+]CC(C)C)C(C)C.[CH2:11]1[CH2:41][O:40][C:13]2([CH2:36][CH2:35][C@@:34]3([CH3:37])[C:15](=[CH:16][CH2:17][C@@H:18]4[C@:33]3([OH:38])[CH2:32][CH2:31][C@@:30]3([CH3:39])[C@H:19]4[CH2:20][CH2:21]/[C:22]/3=[C:23](/[O:28][CH3:29])\[C:24](OC)=[O:25])[CH2:14]2)[O:12]1.O>C1(C)C=CC=CC=1>[CH2:41]1[CH2:11][O:12][C:13]2([CH2:36][CH2:35][C@@:34]3([CH3:37])[C:15](=[CH:16][CH2:17][C@@H:18]4[C@:33]3([OH:38])[CH2:32][CH2:31][C@@:30]3([CH3:39])[C@H:19]4[CH2:20][CH2:21]/[C:22]/3=[C:23](/[O:28][CH3:29])\[CH2:24][OH:25])[CH2:14]2)[O:40]1

Participants

Conditions

Temperature: -20 °C

Procedure

Under nitrogen a 1M solution of diisobutylaluminium hydride in toluene (0.1 ml) was added to a stirred solution of methyl (20Z)-3,3-ethylenedioxy-9α-hydroxy-20-methoxypregna-5,17(20)-dien-21-oate (112 mg, prepared according to Example 19) in dry toluene (8 ml) at -20° C. The reaction mixture was stirred at -20° C. for 30 minutes. To complete the reaction the same quantity of diisobutylaluminium hydride solution was added and stirring was continued at -20° C. for 5 minutes. Next, water (2 ml) was added and the mixture was stirred at 0° C. for 1 hour. The heterogeneous mixture was filtered, then the filtrate was concentrated under reduced pressure to afford 66 mg of the title compound as a white solid.

Workup

additionwas added
stirringstirring
waitwas continued at -20° C. for 5 minutes
stirringthe mixture was stirred at 0° C. for 1 hour
filtrationThe heterogeneous mixture was filtered
concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record: ord-97d20b7a5ee54fab93b674a346f424ce
Source dataset: uspto-grants-1993_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05194602

Reaction notes

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