3-Methylpyridine-2-carboxaldehyde → {3-[(3-Methyl-pyridin-2-ylmethyl)-(1-pyridin-2-yl-ethyl)-amino]-propyl}-carbamic acid tert-butyl ester

HRID 251097Notes

Reaction equation

HRID 251097 reaction equation
[C:1]([O:5][C:6](=[O:20])[NH:7][CH2:8][CH2:9][CH2:10][NH:11][CH:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)[CH3:13])([CH3:4])([CH3:3])[CH3:2].[CH3:21][C:22]1[C:23]([CH:28]=O)=[N:24][CH:25]=[CH:26][CH:27]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:20])[NH:7][CH2:8][CH2:9][CH2:10][N:11]([CH2:28][C:23]1[C:22]([CH3:21])=[CH:27][CH:26]=[CH:25][N:24]=1)[CH:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)[CH3:13])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 15018743-Methylpyridine-2-carboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 67272175[3-(1-Pyridin-2-yl-ethylamino)-propyl]-carbamic acid tert-butyl ester

Product 1

HCID 67273022{3-[(3-Methyl-pyridin-2-ylmethyl)-(1-pyridin-2-yl-ethyl)-amino]-propyl}-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using General Procedure B: Reaction of [3-(1-pyridin-2-yl-ethylamino)-propyl]-carbamic acid tert-butyl ester and 3-methyl-pyridine-2-carboxaldehyde with NaBH(OAc)3 in CH2Cl2 gave {3-[(3-methyl-pyridin-2-ylmethyl)-(1-pyridin-2-yl-ethyl)-amino]-propyl}-carbamic acid tert-butyl ester as a colorless oil.

Sources & evidence

ORD record
ord-c581c2e963814d69bd66612820ad825c
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

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