Dimethyl Sulfide → (S)-2,2,2-trifluoro-1-(7-hydroxy-1,2,7,8,9,10-hexahydrobenzo[f]isoquinolin-3(4H)-yl)ethanone
Reaction equation
B1(C)OC(C2C=CC=CC=2)(C2C=CC=CC=2)[C@@H]2N1CCC2.S(C)C.[F:25][C:26]([F:45])([F:44])[C:27]([N:29]1[CH2:38][CH2:37][C:36]2[C:35]3[CH2:39][CH2:40][CH2:41][C:42](=[O:43])[C:34]=3[CH:33]=[CH:32][C:31]=2[CH2:30]1)=[O:28]>C1(C)C=CC=CC=1.C1COCC1>[F:45][C:26]([F:25])([F:44])[C:27]([N:29]1[CH2:38][CH2:37][C:36]2[C:35]3[CH2:39][CH2:40][CH2:41][C@H:42]([OH:43])[C:34]=3[CH:33]=[CH:32][C:31]=2[CH2:30]1)=[O:28]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of (R)-2-methyl-CBS-oxazaborolidine (1M solution in toluene, 0.1 mL, 0.1 mmol) in 3 mL of toluene at −10 ° C. was added BH3.SMe2 (0.23 mL, 2.4 mmol). To this stirred solution was then added 3-(2,2,2-trifluoroacetyl)-1,2,3,4,9,10-hexahydrobenzo[f]isoquinolin-7(8H)-one (594 mg, 2 mmol)in 5 mL of dry THF dropwise while keeping the temperature around −10° C. After stirring at room temperature for 2 h, the reaction mixture was cooled down to −5 ° C. and was quenched with 1 ML of MeOH and was then evaporated to dryness and directly submitted to flash chomatography (SiO2, hexane/EtOAc=2:1 to 1:1) to afford (S)-2,2,2-trifluoro-1-(7-hydroxy-1,2,7,8,9,10-hexahydrobenzo[f]isoquinolin-3(4H)-yl)ethanone as a white solid.
Workup
- customthe temperature around −10° C
- temperaturethe reaction mixture was cooled down to −5 ° C.
- customwas quenched with 1 ML of MeOH
- customwas then evaporated to dryness
Sources & evidence
- ORD record
- ord-e03500922c0d43e098f40aa11b784284
- Source dataset
- uspto-grants-2010_02
- Patent number
- US07662811B2
Reaction notes
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