Methyl chloroformate → ST50924908

HRID 2307407Notes

Reaction equation

HRID 2307407 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[CH2:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:8][NH:7]1.C(N(CC)CC)C>C(Cl)Cl>[CH3:5][O:4][C:2]([N:7]1[CH2:8][CH2:9][C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:6]1)=[O:3]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 70461,2,3,4-TetrahydroisoquinolineHCID 8471Triethylamine

Product 1

HCID 3441966ST50924908Yield 99.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of methyl chloroformate (15.45 mL, 200 mmol) in CH2Cl2 (50 mL) was added to a solution of 1,2,3,4-tetrahydroisoquinoline (13.3 g, 100 mmol) and triethylamine (57 mL, 400 mmol) in CH2Cl2 (200 mL) at 0° C. The reaction mixture was stirred for 3 hours then was quenched with water. The organic layer was separated and washed with water (2×50 mL). The organic layer was then dried over anhydrous magnesium sulfate, filtered and the resultant filtrate was concentrated in vacuo to provide the title compound (19.1 g). The crude material thus obtained was used without further purification.

Workup

  1. customthen was quenched with water
  2. customThe organic layer was separated
  3. washwashed with water (2×50 mL)
  4. dry with materialThe organic layer was then dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe resultant filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-c13effe7e0524f3482a208749a8fa67d
Source dataset
uspto-grants-2004_12
Patent number
US06831080B2

Reaction notes

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