Dimethyl Sulfide → (S)-2,2,2-trifluoro-1-(6-hydroxy-3,4,6,7,8,9-hexahydrobenzo[g]isoquinolin-2(1H)-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:31](=[CH:32][C:33]3[CH2:42][CH2:41][CH2:40][C:39](=[O:43])[C:34]=3[CH:35]=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:31](=[CH:32][C:33]3[CH2:42][CH2:41][CH2:40][C@H:39]([OH:43])[C:34]=3[CH:35]=2)[CH2:30]1)=[O:28]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of (R)-2-methyl-CBS-oxazaborolidine (1M solution in toluene, 0.56 mL, 0.56 mmol) in 15 mL of toluene at −10° C. was added BH3.SMe2 (1.27 mL, 13.38 mmol). To this stirred solution was then added 2-(2,2,2-trifluoroacetyl)-1,2,3,4,8,9-hexahydrobenzo[g]-isoquinolin-6(7H)-one(3.31 g, 11.15 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 −10° C. and was quenched with 6 mL of MeOH and was then evaporated to dryness and directly submitted to flash chomatography (SiO2, hexane/EtOAc=3:1 to 2:1 to 1:1) to afford (S)-2,2,2-trifluoro-1-(6-hydroxy-3,4,6,7,8,9-hexahydrobenzo[g]isoquinolin-2(1H)-yl)ethanone as a white solid.
Workup
- customthe temperature around −10° C
- temperaturethe reaction mixture was cooled down to −10° C.
- customwas quenched with 6 mL of MeOH
- customwas then evaporated to dryness
Sources & evidence
- ORD record
- ord-d056fd2f40d643ccaec1ea1b35019816
- Source dataset
- uspto-grants-2010_02
- Patent number
- US07662811B2
Reaction notes
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