Water → HCID 11473847, compound
Reaction equation
[C:1]([O:5][C:6]([N:8]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C@@H:9]([CH2:14][CH2:15][CH2:16][C:17](OC)=[O:18])[C:10]([O:12][CH3:13])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(C[Al]CC(C)C)C.O>C(OCC)C>[C:24]([O:23][C:21]([N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C@H:9]([C:10]([O:12][CH3:13])=[O:11])[CH2:14][CH2:15][CH2:16][CH:17]=[O:18])=[O:22])([CH3:26])([CH3:27])[CH3:25]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -70 °C
Procedure
To a solution of the material from Step 2 (7.51 g, 19.08 mmol) in diethyl ether (95 mL) at −78° C. was slowly added 1.0 M Dibal-H (26.7 mL, 26.7 mmol) in hexanes. The reaction mixture was stirred at −70° C. for 90 minutes. Water (10 mL) was slowly added, and the reaction mixture was allowed to warm up to room temperature and aged for 30 minutes. Additional water (20 mL) was added, aged for 10 minutes with vigorous stirring. 8 g of celite was added to the reaction mixture, aged at room temperature for 5 minutes, filtered on a short pad of celite, rinsed with tert-butyl methyl ether (10×). The filtrate was washed with brine, dried over MgSO4, filtered and concentrated in vacuo to afford 7.06 g of the title compound that was used without further purification.
Workup
- customat −78° C.
- temperatureto warm up to room temperature and aged for 30 minutes
- waitaged for 10 minutes with vigorous stirring
- addition8 g of celite was added to the reaction mixture
- waitaged at room temperature for 5 minutes
- filtrationfiltered on a short pad of celite
- washrinsed with tert-butyl methyl ether (10×)
- washThe filtrate was washed with brine
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-fc325a9ecfb040838d28cad713c4359c
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09079834B2
Reaction notes
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