Morpholine → (S)-tert-Butyl 3-(morpholinomethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

HRID 528870Notes

Reaction equation

HRID 528870 reaction equation
[CH:1]([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][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=O.[NH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1>>[O:23]1[CH2:24][CH2:25][N:20]([CH2:1][C@@H:3]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH2:5][N:4]2[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:21][CH2:22]1

Participants

3

Reactant 2

HCID 8083MorpholineHCID 22861260(S)-tert-Butyl 3-formyl-3,4-dihydroisoquinoline-2(1H)-carboxylate

Product 1

HCID 86718896(S)-tert-Butyl 3-(morpholinomethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylateYield 89.1%

Procedure

Following a procedure analogous to that for the synthesis of Example 106, (S)-tert-butyl 3-formyl-3,4-dihydroisoquinoline-2(1H)-carboxylate (Aubry, S. et al., Tetrahedron Lett., 47:1319-1323 (2006)) (71 mg, 0.27 mmol) and morpholine (28 μL, 0.33 mmol) were converted to the title compound (80 mg, 89%). 1H NMR (CDCl3, mixture of rotamers) δ 7.24-7.20 (m, 4H), 4.85-4.66 (m, 1H), 4.54-4.42 (m, 1H), 4.30-4.17 (m, 1H), 3.67 (br s, 4H), 3.13-2.96 (m, 1H), 2.93-2.69 (m, 1H), 2.62-2.29 (m, 5H), 2.18-2.01 (m, 1H), 1.51 (s, 9H); MS(ESI+) m/z 333.2 (M+H)+.

Sources & evidence

ORD record
ord-825b558604464bb0b50acb2fe5df7f7a
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

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