6-Methoxyisoquinoline-3-carboxylic acid → 6-Isopropoxy-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid

HRID 1845005Notes

Reaction equation

HRID 1845005 reaction equation
CO[C:3]1[CH:4]=C2C(=C[CH:12]=1)C=NC(C(O)=O)=C2.C[O:17][C:18]([CH:20]1[CH2:29][C:28]2[C:23](=[CH:24][CH:25]=[C:26]([OH:30])[CH:27]=2)[CH2:22][N:21]1C(OC(C)(C)C)=O)=[O:19]>>[CH:3]([O:30][C:26]1[CH:27]=[C:28]2[C:23](=[CH:24][CH:25]=1)[CH2:22][NH:21][CH:20]([C:18]([OH:17])=[O:19])[CH2:29]2)([CH3:4])[CH3:12]

Participants

3

Reactant 2

HCID 573069496-Methoxyisoquinoline-3-carboxylic acidHCID 577645552-tert-Butyl 3-methyl 6-hydroxy-3,4-dihydroisoquinoline-2,3(1H)-dicarboxylate

Product 1

HCID 669405386-Isopropoxy-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acidYield 9.1%

Procedure

0.2 g (9.1%, 4 steps) of the 6-isopropoxy-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid was prepared according to procedure described for the synthesis of 6-methoxy-isoquinoline-3-carboxylic acid (in Example 294) starting from 0.67 g (2.18 mmol) of 6-hydroxy-3,4-dihydro-1H-isoquinoline-2,3-dicarboxylic acid 2-tert-butyl ester 3-methyl ester. LCMS: 232 (M+1)+.

Sources & evidence

ORD record
ord-36403f02ba9942368f254034f918ad87
Source dataset
uspto-grants-2015_02
Patent number
US08946259B2

Reaction notes

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