Triethylamine → HCID 86760160, compound

HRID 1792234Notes

Reaction equation

[Si:1]([O:8][C@@H:9]1[C@@:26]2([CH3:27])[C:13](=[CH:14][CH:15]=[C:16]3[C@@H:25]2[CH2:24][CH2:23][C@@:21]2([CH3:22])[C@H:17]3[CH2:18][CH2:19][C@@H:20]2[CH2:28][OH:29])[CH2:12][C@@H:11]([O:30][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:45][S:46](Cl)(=[O:48])=[O:47]>O1CCCC1.CCCCCC>[Si:1]([O:8][C@@H:9]1[C@@:26]2([CH3:27])[C:13](=[CH:14][CH:15]=[C:16]3[C@@H:25]2[CH2:24][CH2:23][C@@:21]2([CH3:22])[C@H:17]3[CH2:18][CH2:19][C@@H:20]2[CH2:28][O:29][S:46]([CH3:45])(=[O:48])=[O:47])[CH2:12][C@@H:11]([O:30][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:32])[CH3:33])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 1α,3β-bis(tert-butyldimethylsilyloxy)-17β-(hydroxymethyl)androsta-5,7-diene (150 mg, 0.274 mmol) and triethylamine (0.153 ml, 1.10 mmol) in tetrahydrofuran (2.3 ml) was cooled to 0° C., followed by the addition of methanesulfonyl chloride (63 μl, 0.814 mmol) and stirring at 0° C. for 1 hour. The reaction mixture was diluted with hexane, washed with water and saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure to remove the solvent. The thus obtained residue was purified by column chromatography (hexane:ethyl acetate=9:1) to give the titled compound (155 mg, 91%) as a colorless foam.

Workup

washwashed with water and saturated brine
dry with materialdried over anhydrous magnesium sulfate
customevaporated under reduced pressure
customto remove the solvent
customThe thus obtained residue was purified by column chromatography (hexane:ethyl acetate=9:1)

Sources & evidence

ORD record: ord-4b7011ffb0c84fa6b7126d0ffa4f7f41
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07074777B2

Reaction notes

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