Benzene, ((2-bromoethoxy)methyl)- → (S)-1-(3-((2-(Benzyloxy)ethoxy)methyl)-3,4-dihydroisoquinolin-2(1H)-yl)ethanone

HRID 528878Notes

Reaction equation

HRID 528878 reaction equation
[OH:1][CH2:2][C@@H:3]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][N:4]1[C:13](=[O:15])[CH3:14].Br[CH2:17][CH2:18][O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[CH2:20]([O:19][CH2:18][CH2:17][O:1][CH2:2][C@@H:3]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][N:4]1[C:13](=[O:15])[CH3:14])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

3

Reactant 2

HCID 73833Benzene, ((2-bromoethoxy)methyl)-HCID 86718900(S)-1-(3-(Hydroxymethyl)-3,4-dihydroisoquinolin-2(1H)-yl)ethanone2×

Product 1

HCID 86718902(S)-1-(3-((2-(Benzyloxy)ethoxy)methyl)-3,4-dihydroisoquinolin-2(1H)-yl)ethanoneYield 65%

Procedure

Following a procedure analogous to that for the synthesis of Intermediate 116B, (S)-1-(3-(hydroxymethyl)-3,4-dihydroisoquinolin-2(1H)-yl)ethanone (Intermediate 116A, 40.0 mg, 0.20 mmol) and ((2-bromoethoxy)methyl)benzene (92 μl, 0.58 mmol) were converted to the title compound (43 mg, 65%) after purification by flash column chromatography (gradient from 0% to 50% EtOAc/hexanes). 1H NMR (CDCl3, 2:1 mixture of amide rotamers) δ 7.41-7.25 (m, 5H), 7.24-7.06 (m, 4H), 5.10 (d, J=18.0 Hz, 1H), 4.66-4.44 (m, 3H), 4.39 (q, J=5.9 Hz, 0.5H), 4.26 (d, J=17.8 Hz, 0.5H), 3.68-3.47 (m, 5H), 3.44-3.27 (m, 1.5H), 3.10 (dd, J=5.8, 16.0 Hz, 0.5H), 3.01-2.80 (m, 1H), 2.24 (s, 2H), 2.19 (s, 1H); MS(ESI+) m/z 340.2 (M+H)+.

Sources & evidence

ORD record
ord-3cc12433e7434aba84a38bc1f915751a
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

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