Water → HCID 68490282, compound

HRID 1944224Notes

Reaction equation

HRID 1944224 reaction equation
C(O)(=O)C.[CH2:5]([O:7][C:8]1[CH:17]=[C:16]2[C:11]([CH2:12][CH2:13][NH:14][CH2:15]2)=[CH:10][C:9]=1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH3:6].CCN(C(C)C)C(C)C.[CH3:35][O:36][C:37]1[CH:38]=[C:39]([CH:42]=[C:43]([O:47][CH3:48])[C:44]=1[O:45][CH3:46])[CH2:40]Cl.O>CN(C=O)C.C(OCC)(=O)C>[CH2:5]([O:7][C:8]1[CH:17]=[C:16]2[CH:11]([CH2:12][CH2:13][N:14]([CH2:40][C:39]3[CH:42]=[C:43]([O:47][CH3:48])[C:44]([O:45][CH3:46])=[C:37]([O:36][CH3:35])[CH:38]=3)[CH2:15]2)[CH2:10][C:9]=1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH3:6]

Participants

7

Reactant 4

HCID 962WaterHCID 774485-(Chloromethyl)-1,2,3-trimethoxybenzeneHCID 81531DiisopropylethylamineHCID 68494147HCID 68494147, compound

Product 1

HCID 68490282HCID 68490282, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 7-ethoxy-6-benzyloxytetrahydroisoquinoline acetate (293 mg, 0.86 mmol), Hunig's base (0.325 mL, 1.96 mmol) and 3,4,5-trimethoxybenzyl chloride (247 mg, 1.14 mmol) in DMF (8 mL) were heated to 80° C. overnight. Water and ethyl acetate (50 mL each) were then added to the cooled solution, the organic layer separated and washed with water (5×), brine, dried and evaporated. The desired product was isolated by column chromatography (3:2 hexane/ethyl acetate) to give the product as a clear colourless oil (340 mg, 85%) which showed 1H NMR δ 1.41 (3H, t, J 7.0), 2.63-2.80 (4H, m), 3.54 (2H, s), 3.58 (2H, s), 3.84 (3H, s), 3.84 (6H, s), 4.03 (2H, q, J 7.0), 5.09 (2H, s), 6.54 (1H, s), 6.61 (2H, s), 6.65 (1H, s) and 7.26-7.44 (5H, m). m/z HRMS [ES+] found 464.2413, C28H34NO5 (M++H) requires 464.2437.

Workup

  1. customthe organic layer separated
  2. washwashed with water (5×), brine
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-cdd49f21c34341fd96e595f58562e3fb
Source dataset
uspto-grants-2013_03
Patent number
US08394825B2

Reaction notes

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