Tetrahydrofuran → (S)-5-Bromo-2-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-1,2,3,4-tetrahydroisoquinoline

HRID 1890726

Reaction equation

Cl.[Br:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][NH:7][CH2:8]2.CCN([CH:19]([CH3:21])[CH3:20])C(C)C.[BH-](OC(C)=O)(OC(C)=O)[O:23]C(C)=O.[Na+].[CH2:36]1C[O:39][CH2:38][CH2:37]1>C(OCC)(=O)C>[Br:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][N:7]([CH2:36][C@H:37]1[CH2:38][O:39][C:19]([CH3:20])([CH3:21])[O:23]1)[CH2:8]2

Participants

Conditions

Temperature: 45 °C

Procedure

A mixture containing 5-bromo-1,2,3,4-tetrahydroisoquinoline hydrochloride (249 mg, 1 mmol), (R)-(+)-2,2-dimethyl-1,3-dioxolane-4-carboxyaldehyde (260 mg, 2 mmol), DIEA (0.2 ml, 1 mmol) and Na(OAc)3BH (440 mg, 2 mmol) in THF (1 ml) is heated at 45° C. for 18 hours. After cooling to room temperature, the reaction mixture is diluted with ethyl acetate. The organic layer is washed with saturated aqueous NaHCO3 solution, water, brine, dried over MgSO4 and concentrated to dryness by rotary evaporation. The crude product is purified by silica gel flash chromatography, eluted with 30% ethyl acetate in dichloromethane to yield (S)-5-Bromo-2-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-1,2,3,4-tetrahydroisoquinoline as a brown oil. LC-MS m/z: 326.1 (M+1).

Workup

temperatureAfter cooling to room temperature
washThe organic layer is washed with saturated aqueous NaHCO3 solution, water, brine
dry with materialdried over MgSO4
concentrationconcentrated to dryness by rotary evaporation
customThe crude product is purified by silica gel flash chromatography
washeluted with 30% ethyl acetate in dichloromethane

Sources & evidence

ORD record: ord-8d145e2c4a544ec4826e0e26586ed956
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08507491B2

Linked notes

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