tert-butyl (2S)-2-(2-hydroxyethyl)pyrrolidine-1-carboxylate → (2S)-1-tert-butoxycarbonyl-2-(2-(1-amino-isoquinolin-6-oxy)-ethyl)-pyrrolidine

HRID 1070565Notes

Reaction equation

HRID 1070565 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[CH2:10][CH2:11][OH:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:16][C:17]1[C:26]2[C:21](=[CH:22][C:23](O)=[CH:24][CH:25]=2)[CH:20]=[CH:19][N:18]=1>ClCCl.CO>[C:1]([O:5][C:6]([N:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[CH2:10][CH2:11][O:12][C:23]1[CH:22]=[C:21]2[C:26](=[CH:25][CH:24]=1)[C:17]([NH2:16])=[N:18][CH:19]=[CH:20]2)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 7062399tert-butyl (2S)-2-(2-hydroxyethyl)pyrrolidine-1-carboxylateHCID 1357539911-Aminoisoquinolin-6-ol

Product 1

HCID 20794988(2S)-1-tert-butoxycarbonyl-2-(2-(1-amino-isoquinolin-6-oxy)-ethyl)-pyrrolidine

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

This compound was prepared from N-tert-butoxycarbonyl-L-β-homoprolinol [Leyendecker, F.; Jesser, F.; Laucher, D.; Tetrahedron Lett. 1983, 24, 3513-3516; 590 mg, 2.75 mmol] and 1-amino-6-hydroxy-isoquinoline (1e, 320 mg, 2.0 mmol) by the Mitsunobu procedure described in Example 1f. Yield: 650 mg (91%). ESI-MS: 358.0 (M+H)+. Rf (silica gel; dichloromethane/methanol, 9:1, v/v): 0.37.

Sources & evidence

ORD record
ord-09f61dd1f2db496881548e582cf4b2ff
Source dataset
uspto-grants-2005_06
Patent number
US06903107B1

Reaction notes

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