HCID 22872556, compound → HCID 53719778, compound
Reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[CH2:12]([O:14][CH2:15][O:16][C@H:17]1[CH2:43][CH2:42][C@@:41]2([CH3:44])[C@@H:19]([C@@H:20]([OH:46])[CH2:21][C@@H:22]3[C@@H:40]2[CH2:39][CH2:38][C@@:37]2([CH3:45])[C@H:23]3[CH2:24][C@@H:25]3[O:30][C@@:29]4([O:36][CH2:35][C@H:33]([CH3:34])[CH2:32][CH2:31]4)[C@@H:27]([CH3:28])[C@@H:26]32)[CH2:18]1)[CH3:13]>>[CH2:12]([O:14][CH2:15][O:16][C@H:17]1[CH2:43][CH2:42][C@@:41]2([CH3:44])[C@@H:19]([C:20](=[O:46])[CH2:21][C@@H:22]3[C@@H:40]2[CH2:39][CH2:38][C@@:37]2([CH3:45])[C@H:23]3[CH2:24][C@@H:25]3[O:30][C@@:29]4([O:36][CH2:35][C@H:33]([CH3:34])[CH2:32][CH2:31]4)[C@@H:27]([CH3:28])[C@@H:26]32)[CH2:18]1)[CH3:13]Participants
3
Procedure
Pyridinium chlorochromate (1.98 g, 9.20 mmol) was added to a mixture of (3β,5α,6α,25R)-3-ethoxy methoxy-6-hydroxyspirostane (0.90 g, 1.8 mmol) and celite (8.0 g) in anhydrous dichloremethane at 0° C. The reaction mixture was gradually warmed to ambient temperature over 1 hour and allowed to stir for an additional 5 hours. The reaction mixture was then filtered through a plug of silica gel using ether as the eluent. The combined ether fractions were concentrated in vacuo to afford 0.80 g (91%) of the title compound as a colorless solid.
Workup
- filtrationThe reaction mixture was then filtered through a plug of silica gel
- concentrationThe combined ether fractions were concentrated in vacuo
Sources & evidence
- ORD record
- ord-b14e61d9cce24638bd6c8e596616a512
- Source dataset
- uspto-grants-1997_12
- Patent number
- US05703052
Reaction notes
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