Hydrochloric Acid → tert-butyl 3-[(1S)-1-hydroxypropyl]benzoate
Reaction equation
C(N(CCCC)[C@H:6]([CH3:15])[C@H:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[OH:8])CCC.C(C1C=C(C=CC=1)[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=O.C([Zn]CC)C.[Cl-].[NH4+].Cl>C1(C)C=CC=CC=1.CCCCCC>[OH:8][C@H:7]([C:9]1[CH:10]=[C:11]([CH:12]=[CH:13][CH:14]=1)[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:6][CH3:15]Participants
8
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Procedure
To the (1S,2R)-2-di-n-butylamino-1-phenyl-1-propanol (200 mg) in toluene (7 ml) solution, tert-butyl 3-formylbenzoate (3 g) in hexane (7 ml) solution was added and the mixture was stirred at room temperature for 20 minutes. Next, diethylzinc in 1N hexane solution (33 ml) was added to the reaction solution under ice cooling and the mixture was stirred at that temperature for 18 hours. Saturated ammonium chloride aqueous solution was added to the reaction solution, the mixture was stirred at 20 minutes, and 1N hydrochloric acid was added. The obtained mixed solution was extracted with ethyl acetate. The organic layer was dried over with anhydrous sodium sulfate, then concentrated to obtain the title compound (3.5 g).
Workup
- stirringthe mixture was stirred at that temperature for 18 hours
- stirringthe mixture was stirred at 20 minutes
- additionThe obtained mixed solution
- extractionwas extracted with ethyl acetate
- dry with materialThe organic layer was dried over with anhydrous sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-4dbc5cbd72634134ac7205d2db6ee9f9
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08049006B2
Reaction notes
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