2-[2-(4-Methoxy-benzyl)-1-oxo-1,2,3,4-tetrahydro-isoquinolin-6-yl]-2-methyl-propionaldehyde → 2-Methyl-2-(1-oxo-1,2,3,4-tetrahydro-isoquinolin-6-yl)-propionaldehyde

HRID 2069818Notes

Reaction equation

COC1C=CC(C[N:8]2[CH2:17][CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:18]([CH3:22])([CH3:21])[CH:19]=[O:20])[CH:14]=3)[C:9]2=[O:23])=CC=1>FC(F)(F)C(O)=O>[CH3:22][C:18]([C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:23])[NH:8][CH2:17][CH2:16]2)([CH3:21])[CH:19]=[O:20]

Participants

Conditions

Temperature: 80 °C

Procedure

2-[2-(4-Methoxy-benzyl)-1-oxo-1,2,3,4-tetrahydro-isoquinolin-6-yl]-2-methyl-propionaldehyde (420 mg, 1.25 mmol) was taken up in trifluoroacetic acid (5 mL) and the resulting mixture was stirred at 80° C. for 2.5 hours and then cooled to room temperature. The trifluoroacetic acid was removed under reduced pressure at 60° C., and then co-evaporated with ethyl acetate (5×). The residue was taken up in ethyl acetate (175 mL) and then washed with water (3×50 mL) and finally with brine (1×50 mL). The ethyl acetate layer was dried over magnesium sulfate, filtered and concentrated to give the crude product. Purification on silica gel eluting with a gradient of 50% ethyl acetate in hexanes to neat ethyl acetate gave the title compound as a white powder (228 mg). MS (ESI) 218.0 (M+H)+.

Workup

temperaturecooled to room temperature
customThe trifluoroacetic acid was removed under reduced pressure at 60° C.
washwashed with water (3×50 mL) and finally with brine (1×50 mL)
dry with materialThe ethyl acetate layer was dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated
customto give the crude product
customPurification on silica gel eluting with a gradient of 50% ethyl acetate in hexanes to neat ethyl acetate

Sources & evidence

ORD record: ord-9531ab8bbf864118ac8e9ff189db352b
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08299077B2

Reaction notes

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