Acetyl chloride → (R)-Methyl 5-bromo-1,2,3,4-tetrahydroisoquinoline-3-carboxylate hydrochloride

HRID 1854546Notes

Reaction equation

HRID 1854546 reaction equation
[C:1]([Cl:4])(=O)C.Cl.[Br:6][C:7]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:8]=1[CH2:9][C@H:10]([C:17]([OH:19])=[O:18])[NH:11][CH2:12]2>CO>[ClH:4].[Br:6][C:7]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:8]=1[CH2:9][C@H:10]([C:17]([O:19][CH3:1])=[O:18])[NH:11][CH2:12]2

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 117720332(R)-5-Bromo-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid hydrochloride

Product 1

HCID 118798131(R)-Methyl 5-bromo-1,2,3,4-tetrahydroisoquinoline-3-carboxylate hydrochlorideYield 100.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dissolve dimethyl (3R)-5-bromo-3,4-dihydro-1H-isoquinoline-2,3-dicarboxylate (27.55 g, 84.0 mmol) in 5N hydrochloric acid (330.6 mL, 1.65 mol) and heat to reflux for three days. Concentrate under reduced pressure to give a white solid. Wash the solid with diethyl ether and dry under vacuum at 40° C. overnight to give (3R)-5-bromo-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid hydrochloride (1:1) (20.8 g, 71.1 mmol). Add acetyl chloride (50.6 mL, 711.0 mmol) to a 0° C. mixture of (3R)-5-bromo-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid hydrochloride (1:1) (20.8 g, 71.1 mmol) in methanol (474 mL). Warm to room temperature and stir for 36 hours. Concentrate under reduced pressure and dry to give the title compound (21.9 g, 71.4 mmol). MS (m/z): 270 (M+1).

Workup

  1. concentrationConcentrate under reduced pressure
  2. customdry

Sources & evidence

ORD record
ord-f25ac91ade04416cb7c21cba17bbc8db
Source dataset
uspto-grants-2015_02
Patent number
US08962654B2

Reaction notes

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