TBAF tetrahydrofuran → 20-{4-ethyl-4-hydroxy-(2Z)-hexenyloxy}-1alpha,3beta-dihydroxy-20-methylpregna-5,7,16-triene

HRID 1792191Notes

Reaction equation

[Si]([O:8][C@@H:9]1[C@@:45]2([CH3:46])[C:13](=[CH:14][CH:15]=[C:16]3[C@@H:44]2[CH2:43][CH2:42][C@@:41]2([CH3:47])[C@H:17]3[CH2:18][CH:19]=[C:20]2[C:21]([O:24]/[CH:25]=[CH:26]\[CH2:27][C:28]([CH2:39][CH3:40])([O:31][Si](CC)(CC)CC)[CH2:29][CH3:30])([CH3:23])[CH3:22])[CH2:12][C@@H:11]([O:48][Si](C(C)(C)C)(C)C)[CH2:10]1)(C(C)(C)C)(C)C.O1CCCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>>[CH2:29]([C:28]([OH:31])([CH2:39][CH3:40])[CH2:27]/[CH:26]=[CH:25]\[O:24][C:21]([CH3:23])([C:20]1[C@:41]2([CH3:47])[C@H:17]([C:16]3[C@H:44]([CH2:43][CH2:42]2)[C@:45]2([CH3:46])[C:13]([CH2:12][C@@H:11]([OH:48])[CH2:10][C@@H:9]2[OH:8])=[CH:14][CH:15]=3)[CH2:18][CH:19]=1)[CH3:22])[CH3:30]

Participants

Reactant 2

HCID 11078149TBAF tetrahydrofuran

HCID 867601481alpha,3beta-bis(tert-butyldimethylsilyloxy)-20-{4-ethyl-4-triethylsilyloxy-(2Z)-hexenyloxy}-20-methylpregna-5,7,16-triene

Product 1

HCID 8676015020-{4-ethyl-4-hydroxy-(2Z)-hexenyloxy}-1alpha,3beta-dihydroxy-20-methylpregna-5,7,16-trieneYield 91%

Procedure

1α,3β-Bis(tert-butyldimethylsilyloxy)-20-{4-ethyl-4-triethylsilyloxy-(2Z)-hexenyloxy}-20-methylpregna-5,7,16-triene (99 mg, 0.122 mmol) and a 1M tetra-n-butylammonium fluoride tetrahydrofuran solution (5 ml) were subjected to reaction using a procedure similar to that of Example 5(2) (3 hours), worked up and purified by column chromatography (ethyl acetate) to give the titled compound (52 mg, 91%) as a colorless glassy substance.

Workup

customof Example 5(2) (3 hours)
custompurified by column chromatography (ethyl acetate)

Sources & evidence

ORD record: ord-d25398eb085f454aac8b21b25e9e69e1
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07074777B2

Reaction notes

Loading…