Dichloromethane → HCID 66935714, compound

HRID 1028208Notes

Reaction equation

HRID 1028208 reaction equation
ClCCl.Cl[C:5]([O:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)=[O:6].[NH2:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[CH2:24][N:23]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:22][CH2:21]2>N1C=CC=CC=1>[C:31]([O:30][C:28]([N:23]1[CH2:22][CH2:21][C:20]2[C:25](=[CH:26][CH:27]=[C:18]([NH:17][C:5]([O:7][C:8]3[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=3)=[O:6])[CH:19]=2)[CH2:24]1)=[O:29])([CH3:34])([CH3:32])[CH3:33]

Participants

5

Reactant 3

HCID 6344Dichloromethane2×HCID 821294-Nitrophenyl chloroformateHCID 27563716-Amino-2-N-Boc-1,2,3,4-tetrahydro-isoquinoline

Product 1

HCID 66935714HCID 66935714, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

To a dichloromethane (10 mL) solution of 4-nitrophenyl chloroformate (812 mg), a dichloromethane (10 mL) solution of 6-amino-2N-Boc-1,2,3,4-tetrahydroisoquinoline (1.00 g) and pyridine (0.33 mL) was gradually added at 0° C. The reaction mixture was stirred at 0° C. for 1 hour and at room temperature for 2 hours and then concentrated. The residue was vigorously stirred in a mixed solution of diisopropyl ether and water (diisopropyl ether/water). The precipitate was collected by filtration and dried under reduced pressure to obtain the title compound (1.46 g, 88%) as a yellow solid.

Workup

  1. concentrationconcentrated
  2. stirringThe residue was vigorously stirred in a mixed solution of diisopropyl ether and water (diisopropyl ether/water)
  3. filtrationThe precipitate was collected by filtration
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-5f4da713ec10418882ad1d1249118da0
Source dataset
uspto-grants-2014_05
Patent number
US08735425B2

Reaction notes

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