Sodium borohydride → 1-(4-(Trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline

HRID 445255Notes

Reaction equation

[F:1][C:2]([F:20])([F:19])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11][N:10]=2)=[CH:5][CH:4]=1.[BH4-].[Na+]>CO>[F:20][C:2]([F:1])([F:19])[C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11][NH:10]2)=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline (4.69 g, 17 mmol) in MeOH (24 mL) was added sodium borohydride (1.94 g, 51.1 mmol) slowly at 0° C. Then, the mixture was stirred at 0° C. for 15 min and at RT for 2 h. The solvent was then removed and H2O (20 mL) was added to the residue. A saturated NaHCO3 solution (150 mL) was added slowly and the mixture was extracted with EtOAc (2×200 mL). The combined organic extracts were dried over MgSO4 and concentrated. The residue was mixed with silica gel (4:1; residue:silica gel) and purified by silica gel chromatography (20%-100% EtOAc/hexane) to give the title compound as a white solid. MS (ESI, positive ion) m/z: 278 (M+H).

Workup

customThe solvent was then removed
additionH2O (20 mL) was added to the residue
additionA saturated NaHCO3 solution (150 mL) was added slowly
extractionthe mixture was extracted with EtOAc (2×200 mL)
dry with materialThe combined organic extracts were dried over MgSO4
concentrationconcentrated
additionThe residue was mixed with silica gel (4:1; residue:silica gel)
custompurified by silica gel chromatography (20%-100% EtOAc/hexane)

Sources & evidence

ORD record: ord-e915530bbd774fc89c538eff496f0229
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08476297B2

Reaction notes

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