tert-Butyl acrylate → Tert-butyl 3-(6-hydroxy-3,4-dihydroisoquinolin-2(1H)-yl)propanoate

HRID 2264555Notes

Reaction equation

HRID 2264555 reaction equation
Br.[CH2:2]1[C:11]2[C:6](=[CH:7][C:8]([OH:12])=[CH:9][CH:10]=2)[CH2:5][CH2:4][NH:3]1.[C:13]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])(=[O:16])[CH:14]=[CH2:15].C(N(C(C)C)C(C)C)C>CO>[OH:12][C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][CH:9]=1)[CH2:2][N:3]([CH2:15][CH2:14][C:13]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:4][CH2:5]2

Participants

5

Reactant 3

HCID 15458tert-Butyl acrylateHCID 81531DiisopropylethylamineHCID 133617991,2,3,4-Tetrahydroisoquinolin-6-ol--hydrogen bromide (1/1)

Product 1

HCID 59595894Tert-butyl 3-(6-hydroxy-3,4-dihydroisoquinolin-2(1H)-yl)propanoateYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1,2,3,4-tetrahydroisoquinolin-6-ol hydrobromide (345 mg, 1.5 mmol), tert-butyl acrylate (0.44 ml, 3.0 mmol) and N-ethyl-N-isopropylpropan-2-amine (2.6 ml, 15.0 mmol) in MeOH was irradiated in the microwave at 90° C. for 1800 s. Removal of the solvents gave the residue which was purified on ISCO column (2% to 5% MeOH/CH2Cl2) to provide the title compounds (332 mg, 80%). 1H NMR (400 MHz, CD3OD) δ 6.85 (d, 1H), 6.55 (dd, 1H), 6.54 (s, 1H), 3.55 (s, 2H), 2.83 (m, 4H), 2.76 (m, 2H), 2.54 (dd, 2H), 1.45 (s, 9H). MS (ESI) m/z: Calculated: 277.17; Observed: 277.90 (M++1).

Workup

  1. customRemoval of the solvents
  2. customgave the residue which
  3. customwas purified on ISCO column (2% to 5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-d9468c0485f54b519f4b3129c9a81021
Source dataset
uspto-grants-2010_12
Patent number
US07855193B2

Reaction notes

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