7-Isoquinolinol → 1,2-Bis(1,1-dimethylethyl) (2S,4S)-4-(7-isoquinolinyloxy)-1,2-pyrrolidinedicarboxylate

HRID 1442963Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([OH:13])[CH2:10][C@H:9]1[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:21]1[C:30]2[C:25](=[CH:26][CH:27]=[C:28](O)[CH:29]=2)[CH:24]=[CH:23][N:22]=1>>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([O:13][C:28]2[CH:29]=[C:30]3[C:25]([CH:24]=[CH:23][N:22]=[CH:21]3)=[CH:26][CH:27]=2)[CH2:10][C@H:9]1[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 2

HCID 4597677-Isoquinolinol

HCID 7408710Di-tert-butyl (2S,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate

Product 1

HCID 591667551,2-Bis(1,1-dimethylethyl) (2S,4S)-4-(7-isoquinolinyloxy)-1,2-pyrrolidinedicarboxylate

Procedure

The title compound was synthesised from (2S,4R)-4-hydroxy-pyrrolidine-1,2-dicarboxylic acid di-tert-butyl ester (CAS Reg. No. 170850-75-6) and isoquinolin-7-ol using the same method as preparation 11 and gave the title compound as an oil in 15% yield.

Sources & evidence

ORD record: ord-0c275a3bfeb54aa38097f7e3875ce0dd
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07659305B2

Reaction notes

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