Hydrochloric Acid → HCID 86623926, compound
Reaction equation
Cl.[CH3:2][NH:3][O:4][CH3:5].C[Al](C)C.[C:10]([O:14][C:15]([C@:17]12[C@@H:22]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C@H:21]1[CH2:20][O:19][C:18]2=[O:29])=[O:16])([CH3:13])([CH3:12])[CH3:11].Cl>ClCCl>[C:10]([O:14][C:15]([C@:17]1([C:18](=[O:29])[N:3]([O:4][CH3:5])[CH3:2])[C@@H:22]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C@H:21]1[CH2:20][OH:19])=[O:16])([CH3:12])([CH3:11])[CH3:13]Participants
Conditions
- Temperature
- 0 °C
Procedure
In a 100 mL round-bottomed flask, a solution of N,O-dimethyl hydroxylamine HCl was suspended in 20 mL of dichloromethane. After cooling to 0° C., trimethyl aluminum (2 M in toluene. 3.83 mL, 7.66 mmol) was added dropwise and the mixture was stirred at 0° C. for 45 min. A solution of the previously described (1R*,5R*,6R*)-2-oxo-6-phenyl-3-oxa-bicyclo[3.1.0]hexane-1-carboxylic acid tert-butyl ester (0.3 g, 1 mmol) in 10 mL of dichloromethane was added dropwise to the cooled stirring solution. After stirring at 0° C. for 5 min, the reaction mixture was warmed to room temperature and stirred for 3 hours. After the reaction was completed, the reaction mixture was again cooled in an ice bath and acidified with 10 mL of 1N HCl, extracted with dichloromethane (×3), dried over MgSO4 and concentrated to afford 0.32 g (86%) of the desired product as a clear oil.
Workup
- stirringstirring solution
- stirringAfter stirring at 0° C. for 5 min
- temperaturethe reaction mixture was warmed to room temperature
- stirringstirred for 3 hours
- temperaturethe reaction mixture was again cooled in an ice bath
- extractionextracted with dichloromethane (×3)
- dry with materialdried over MgSO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-ac8bae9cbdd74b03bc445cf6bc733fd1
- Source dataset
- uspto-grants-2008_04
- Patent number
- US07351825B2
Reaction notes
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