Hydrogen Peroxide → HCID 67226382, compound
Reaction equation
[Si:1]([O:8][C@@H:9]([CH2:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)/[CH:10]=[CH:11]/[C@H:12]1[C@H:16]([O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[CH2:15][C:14](=[O:25])[C@@H:13]1[CH2:26]/[CH:27]=[CH:28]\[CH2:29][CH2:30][CH2:31][C:32]([O:34][CH:35]([CH3:37])[CH3:36])=[O:33])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CCC(C)[BH-](C(C)CC)C(C)CC.[Li+].OO.[Na+].[Cl-]>C1COCC1>[Si:1]([O:8][C@@H:9]([CH2:38][CH2:39][C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)/[CH:10]=[CH:11]/[C@H:12]1[C@H:16]([O:17][Si:18]([C:21]([CH3:22])([CH3:23])[CH3:24])([CH3:19])[CH3:20])[CH2:15][C@H:14]([OH:25])[C@@H:13]1[CH2:26]/[CH:27]=[CH:28]\[CH2:29][CH2:30][CH2:31][C:32]([O:34][CH:35]([CH3:37])[CH3:36])=[O:33])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]Participants
6
Procedure
To a cold solution of crude compound 10b (about 400 g) prepared in EXAMPLE 19 in THF (1.2 L) was added a solution of L-selectride in THF (1 M, 400 mL) with stirring. 30% H2O2 (150 mL) was added at −30° C., the mixture was warmed and then stirred for 0.5 h. Saturated aqueous NaCl (1400 mL) was added and the mixture was extracted twice with MTBE (1 L each), concentrated under reduced pressure. The crude product was purified by column chromatography to give about 120.5 g of compound (11b).
Workup
- temperaturethe mixture was warmed
- stirringstirred for 0.5 h
- extractionthe mixture was extracted twice with MTBE (1 L each)
- concentrationconcentrated under reduced pressure
- customThe crude product was purified by column chromatography
Sources & evidence
- ORD record
- ord-43d494cd720c4f5390fde83d807637ef
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08742143B2
Reaction notes
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