Benzyl Bromide → 7-benzyloxy-3,4-dihydro-1H-isoq uinoline-2,3-dicarboxylic acid 2-tert-butyl ester

HRID 1984832Notes

Reaction equation

HRID 1984832 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@H:17]([C:18]([OH:20])=[O:19])[CH2:16][C:15]2[C:10](=[CH:11][C:12]([OH:21])=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>>[C:1]([O:5][C:6]([N:8]1[CH:17]([C:18]([OH:20])=[O:19])[CH2:16][C:15]2[C:10](=[CH:11][C:12]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 7498Benzyl BromideHCID 6712312(3S)-2-((tert-butoxy)carbonyl)-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

Product 1

HCID 688678577-benzyloxy-3,4-dihydro-1H-isoq uinoline-2,3-dicarboxylic acid 2-tert-butyl esterYield 19.2%

Procedure

2.0 g, (6.8 mmol) of (3S)-7-hydroxy-3,4-dihydro-1H-isoquinoline-2,3-dicarboxylic acid 2-tert-butyl ester was reacted with 2.56 g (15.0 mmol) of benzyl bromide as described in general procedure H. The resulting crude product was subjected to hydrolysis as described in general procedure C. The crude product was purified by column chromatography using 1:1 ethyl acetate and hexane as eluent to afford 0.5 g of 7-benzyloxy-3,4-dihydro-1H-isoq uinoline-2,3-dicarboxylic acid 2-tert-butyl ester.

Workup

  1. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-bd40c1a4fd87491fbff5605eff5083c1
Source dataset
uspto-grants-2009_06
Patent number
US07544699B2

Reaction notes

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