1,2,3,4-Tetrahydroisoquinoline → HCID 67276693, compound

HRID 1695111Notes

Reaction equation

HRID 1695111 reaction equation
[OH:1][C@@H:2]1[CH2:6][N:5]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[C@@H:4]([C:17]([O:19][CH3:20])=[O:18])[CH2:3]1.C1N=CN([C:26]([N:28]2[CH:32]=N[CH:30]=[CH:29]2)=[O:27])C=1.C1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)CCN1>C(Cl)Cl>[CH2:32]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH2:30][CH2:29][N:28]1[C:26]([O:1][C@H:2]1[CH2:3][C@H:4]([C:17]([O:19][CH3:20])=[O:18])[N:5]([C:7]([O:9][CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:8])[CH2:6]1)=[O:27]

Participants

5

Reactant 3

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 682631,1'-CarbonyldiimidazoleHCID 688412HCID 688412, compound

Product 1

HCID 67276693HCID 67276693, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Compound 19 (1.28 g, 4.6 mmol) dissolved in DCM (20 ml) is added dropwise into CDI (0.75 g, 4.6 mmol) solution in DCM (30 ml). After stirring for 2 hr, 1,2,3,4-tetrahydroisoquinoline (0.644 ml, 4.6 mmol) is added and the mixture is stirred over night. The solvent is removed and residue applied to flash chromatography on silica gel (Hex/ethyl acetate, 2/1 to 1/1). Compound 20 (1.8 g, 90%) is obtained as pale yellow syrup.

Workup

  1. stirringthe mixture is stirred over night
  2. customThe solvent is removed

Sources & evidence

ORD record
ord-1ed5137ddbaa45aaa5cecc48a65598af
Source dataset
uspto-grants-2012_04
Patent number
US08163693B2

Reaction notes

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