1-Boc-3-hydroxypiperidine → 6-(Piperidin-3-yloxy)isoquinolin-1-ylamine

HRID 1435967Notes

Reaction equation

HRID 1435967 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([OH:14])[CH2:9]1)=O)(C)(C)C.[NH2:15][C:16]1[C:25]2[C:20](=[CH:21][C:22](O)=[CH:23][CH:24]=2)[CH:19]=[CH:18][N:17]=1>>[NH:8]1[CH2:13][CH2:12][CH2:11][CH:10]([O:14][C:22]2[CH:21]=[C:20]3[C:25](=[CH:24][CH:23]=2)[C:16]([NH2:15])=[N:17][CH:18]=[CH:19]3)[CH2:9]1

Participants

3

Reactant 2

HCID 5456991-Boc-3-hydroxypiperidineHCID 1357539911-Aminoisoquinolin-6-ol

Product 1

HCID 688740866-(Piperidin-3-yloxy)isoquinolin-1-ylamineYield 12.1%

Procedure

This compound was prepared from racemic 3-hydroxypiperidine-1-carboxylic acid tert-butyl ester (207 mg, 1.02 mmol) and 1-amino-6-hydroxyisoquinoline (198 mg, 1.23 mmol) by the Mitsunobu procedure described in 3C, subsequent Boc deprotection according to procedure described in 3D gave racemic 6-(piperidin-3-yloxy)-isoquinolin-1-ylamine (30 mg), El-MS: m/z=244.4 [M+H]+.

Sources & evidence

ORD record
ord-924bf2b344d240cbbe9021fa5901ce97
Source dataset
uspto-grants-2009_11
Patent number
US07618985B2

Reaction notes

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