1,2,3,4-Tetrahydroisoquinoline → 3-carboethoxy-6,7-dimethoxy-N-methyl-1,2,3,4-tetrahydroisoquinoline

HRID 979364Notes

Reaction equation

HRID 979364 reaction equation
[CH2:1]1[C:10]2C(=CC=CC=2)CCN1.[C:11]([CH:14]1[CH2:23][C:22]2[C:17](=[CH:18][C:19]([O:26][CH3:27])=[C:20]([O:24][CH3:25])[CH:21]=2)[CH2:16][N:15]1[CH3:28])([OH:13])=[O:12]>>[C:11]([CH:14]1[CH2:23][C:22]2[C:17](=[CH:18][C:19]([O:26][CH3:27])=[C:20]([O:24][CH3:25])[CH:21]=2)[CH2:16][N:15]1[CH3:28])([O:13][CH2:1][CH3:10])=[O:12]

Participants

3

Reactant 2

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 202022273-carboxy-6,7-dimethoxy-N-methyl-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 202022163-carboethoxy-6,7-dimethoxy-N-methyl-1,2,3,4-tetrahydroisoquinoline

Procedure

The resulting tetrahydroisoquinoline derivative of formula 30 is then esterified with a suitable lower alkanol by standard means to produce a tetrahydroisoquinoline ester of formula 31 (step 2). For example, 3-carboxy-6,7-dimethoxy-N-methyl-1,2,3,4-tetrahydroisoquinoline (30) is treated with HCl in EtOH to produce 3-carboethoxy-6,7-dimethoxy-N-methyl-1,2,3,4-tetrahydroisoquinoline (31).

Sources & evidence

ORD record
ord-ec376af3626944ed8b3b7813ac35f1bc
Source dataset
uspto-grants-1987_05
Patent number
US04667038

Reaction notes

Loading…