proline dl-form → 4-(5-Amino-isoquinoline-6-yloxy)-piperidin-1-carboxylic acid tert-butyl ester

HRID 809597Notes

Reaction equation

HRID 809597 reaction equation
[C:15]([CH3:16])([CH3:17])([CH3:18])[O:19][C:20](=[O:21])[N:22]1[CH2:23][CH2:24][CH:25]([O:28][c:29]2[c:30]([Br:39])[c:31]3[cH:32][cH:33][n:34][cH:35][c:36]3[cH:37][cH:38]2)[CH2:26][CH2:27]1.[CH3:43][CH2:44][O:45][C:46](=[O:47])[CH3:48].[Cu:41][I:42].[N-:11]=[N+:12]=[N-:13].[Na+:14].[Na+:2].[OH-:1].[OH2:40].[OH:3][C:4]([CH:5]1[CH2:8][CH2:7][CH2:6][NH:10]1)=[O:9]>>[NH2:10][c:30]1[c:29]([O:28][CH:25]2[CH2:24][CH2:23][N:22]([C:20]([O:19][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:21])[CH2:27][CH2:26]2)[cH:38][cH:37][c:36]2[c:31]1[cH:32][cH:33][n:34][cH:35]2

Participants

9

Reactant 8

HCID 614proline dl-formHCID 923Sodium ion2×HCID 961HydroxideHCID 962WaterHCID 8857Ethyl AcetateHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 33558AzideHCID 576469744-(5-Bromo-isoquinolin-6-yloxy)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 576469764-(5-Amino-isoquinoline-6-yloxy)-piperidin-1-carboxylic acid tert-butyl ester

Sources & evidence

ORD record
ord-b4b3be053b274cb1b4817e27902f36ab
Source dataset
Test data from https://doi.org/10.1039/C8SC04228D

Reaction notes

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