Triethylamine → 6-Benzyloxy-1-[4-(2-pyrrolidin-1-yl-ethoxy)phenyl]-3,4-dihydro-1H-isoquinoline-2-carboxylic acid ethyl ester

HRID 397058Notes

Reaction equation

HRID 397058 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[CH2:7]([O:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[CH:21]([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33][N:34]3[CH2:38][CH2:37][CH2:36][CH2:35]3)=[CH:27][CH:26]=1)[NH:20][CH2:19][CH2:18]2)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CCN(CC)CC>C1COCC1>[CH2:5]([O:4][C:2]([N:20]1[CH2:19][CH2:18][C:17]2[C:22](=[CH:23][CH:24]=[C:15]([O:14][CH2:7][C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH:16]=2)[CH:21]1[C:25]1[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33][N:34]2[CH2:35][CH2:36][CH2:37][CH2:38]2)=[CH:27][CH:26]=1)=[O:3])[CH3:6]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 181724176-Benzyloxy-1-[4-(2-pyrrolidin-1-yl-ethoxy)phenyl]-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 698756696-Benzyloxy-1-[4-(2-pyrrolidin-1-yl-ethoxy)phenyl]-3,4-dihydro-1H-isoquinoline-2-carboxylic acid ethyl esterYield 143.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl chloroformate (0.017 g, 0.16 mmol), 6-benzyloxy-1-[4-(2-pyrrolidin-1-yl-ethoxy)phenyl]-1,2,3,4-tetrahydroisoquinoline (0.069 g, 0.16 mmol), and Et3N (0.028 ml, 0.20 mmol) in anhydrous THF (10 ml) was stirred at rt under N2 for 20 hr. The reaction mixture was concentrated in vacuo to give 0.115 g of tan solid. Purification by flash chromatography, eluting with EtOAc:MeOH (8:2), gave 0.023 g (28% yield) of white solid.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-cf3c0b418d254c5eb54e220d426615f1
Source dataset
uspto-grants-2003_08
Patent number
US06608203B2

Reaction notes

Loading…