Reaktion #338315

ord-3b24820f47d94e6e8d09a1cacdf2a685

Reaktionsgleichung

Cc1cnc(CNC2CCN(C(=O)OC(C)(C)C)CC2)c(C)c1
4-[(3,5-Dimethyl-pyridin-2-ylmethyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester
O=Cc1nccc2ccccc12
1-isoquinoline-carbaldehyde
CC(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]
NaBH(OAc)3
→
Cc1cnc(CN(Cc2nccc3ccccc23)C2CCN(C(=O)OC(C)(C)C)CC2)c(C)c1
4-[(3,5-Dimethyl-pyridin-2-ylmethyl)-isoquinolin-1-ylmethyl-amino]-piperidine-1-carboxylic acid tert-butyl ester

Edukte

Cc1cnc(CNC2CCN(C(=O)OC(C)(C)C)CC2)c(C)c1
4-[(3,5-Dimethyl-pyridin-2-ylmethyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester
O=Cc1nccc2ccccc12
1-isoquinoline-carbaldehyde
CC(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]
NaBH(OAc)3

Reagenzien

Keine

Lösungsmittel

ClCCl
CH2Cl2

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

Using General Procedure B: Reaction of 4-[(3,5-Dimethyl-pyridin-2-ylmethyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester and 1-isoquinoline-carbaldehyde with NaBH(OAc)3 in CH2Cl2 gave 4-[(3,5-Dimethyl-pyridin-2-ylmethyl)-isoquinolin-1-ylmethyl-amino]-piperidine-1-carboxylic acid tert-butyl ester as a colorless oil. Deprotection with TFA using General Procedure F gave (3,5-Dimethyl-pyridin-2-ylmethyl)-isoquinolin-1-ylmethyl-piperidin-4-yl-amine as a white foam.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07863293B2uspto-grants-2011_01