Methyl chloroformate → HCID 22132535, compound

HRID 1856790Notes

Reaction equation

HRID 1856790 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][NH:8][CH2:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[C:20]([O:22][CH3:23])=[O:21].C(OCC)(=O)C.CCCCCC>ClCCl>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([C:20]([O:22][CH3:23])=[O:21])[CH2:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 107292557-Bromo-1,2,3,4-tetrahydroisoquinolineHCID 21226206Ethyl acetate hexane

Product 1

HCID 22132535HCID 22132535, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 7-bromo-1,2,3,4-tetrahydroisoquinoline (19.33 g, 0.091 mol) and triethylamine (16.6 ml, 0.119 mol) in dichloromethane (300 ml) was added a solution of methyl chloroformate (8.5 ml; 0.109 mol) in dichloromethane (30 ml), dropwise with ice cooling. Mixture was stirred for 3 h at room temperature then partitioned between saturated aqueous NaHCO3 (100 ml) and dichloromethane (100 ml). Organic phase was dried (Na2SO4) and evaporated in vacuo to give an oil. Chromatography on silica with 30% ethyl acetate-hexane as eluant gave the title compound as an oil (15.25 g, 62%).

Workup

  1. customthen partitioned between saturated aqueous NaHCO3 (100 ml) and dichloromethane (100 ml)
  2. dry with materialOrganic phase was dried (Na2SO4)
  3. customevaporated in vacuo
  4. customto give an oil

Sources & evidence

ORD record
ord-e3f14d3fefbe499f8119f368cc1861b1
Source dataset
uspto-grants-2000_11
Patent number
US06143762

Reaction notes

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