Methanol → 1,2,3,4-Tetrahydroisoquinolin-6-ol

HRID 1633877Notes

Reaction equation

HRID 1633877 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH2:13][NH:12][CH2:11][CH2:10]2.CO>ClCCl>[CH2:13]1[C:14]2[C:9](=[CH:8][C:7]([OH:6])=[CH:16][CH:15]=2)[CH2:10][CH2:11][NH:12]1

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 393566-Methoxy-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 266981,2,3,4-Tetrahydroisoquinolin-6-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of boron tribromide (1.2 mL, 12.5 mmol) in dichloromethane (12.5 mL) was added dropwise to a −78° C. solution of 6-methoxytetrahydroisoquinoline (1.0 g, 5.0 mol, prepared as described in Org. Synth 1988, 67, 60) in dichloromethane (38 mL) The mixture was stirred for 1 hour, warmed to 0° C., stirred for 1 hour, warmed to room temperature, and stirred for 1 hour. The mixture was cooled to −78° C., treated dropwise with methanol (20 mL), warmed to room temperature, stirred for 1 hour, and concentrated to provide the desired product.

Workup

  1. stirringstirred for 1 hour
  2. temperaturewarmed to room temperature
  3. stirringstirred for 1 hour
  4. temperatureThe mixture was cooled to −78° C.
  5. temperaturewarmed to room temperature
  6. stirringstirred for 1 hour
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f2b4f9fad9b942a7a0138e227eb21ae1
Source dataset
uspto-grants-2003_01
Patent number
US06504031B1

Reaction notes

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