Triethylamine → HCID 86615373, compound

HRID 1436488Notes

Reaction equation

HRID 1436488 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]2[C:3]=1[CH2:4][C@H:5]([CH2:21][OH:22])[N:6]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:7]2.C(N(CC)CC)C>CS(C)=O>[Br:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]2[C:3]=1[CH2:4][C@H:5]([CH:21]=[O:22])[N:6]([C:14]([O:16][C:17]([CH3:18])([CH3:20])[CH3:19])=[O:15])[CH2:7]2

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 69016586HCID 69016586, compound

Product 1

HCID 86615373HCID 86615373, compoundYield 97.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve the tert-butyl 5-bromo-3(R)-(hydroxymethyl)-8-methoxy-3,4-dihydroisoquinoline-2(1H)-carboxylate (710 mg, 0.0019 mol) in dimethylsulfoxide (2.00 mL) and cool to 0° C. Add triethylamine (1.06 mL, 0.00763 mol) and sulfur trioxide-pyridine complex (0.607 g, 0.00381 mol). Warm to room temperature over one hour. Dilute diethyl ether (100 mL) and extract (3×25 mL) with 5% aqueous citric acid, (1×25 mL) saturated aqueous sodium chloride, and dry over magnesium sulfate. Concentrate the filtrate to give the desired product (687 mg, 94%) as an off-white semi-solid.

Workup

  1. temperatureWarm to room temperature over one hour
  2. extractionDilute diethyl ether (100 mL) and extract (3×25 mL) with 5% aqueous citric acid, (1×25 mL) saturated aqueous sodium chloride
  3. dry with materialdry over magnesium sulfate
  4. concentrationConcentrate the filtrate

Sources & evidence

ORD record
ord-d67e986668a948d08375edce7c4de9c4
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

Loading…