(3-Methylpyridin-2-yl)methanamine → (Tert-butoxycarbonylimino-{4-[(3-methyl-pyridin-2-ylmethyl)-amino]-piperidin-1-yl}-methyl)-carbamic acid tert-butyl ester

HRID 251112Notes

Reaction equation

HRID 251112 reaction equation
[C:1]([O:5][C:6](=[O:24])[NH:7][C:8](=[N:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[N:9]1[CH2:14][CH2:13][C:12](=O)[CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2].[CH3:25][C:26]1[C:27]([CH2:32][NH2:33])=[N:28][CH:29]=[CH:30][CH:31]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:24])[NH:7][C:8](=[N:16][C:17]([O:19][C:20]([CH3:22])([CH3:23])[CH3:21])=[O:18])[N:9]1[CH2:10][CH2:11][CH:12]([NH:33][CH2:32][C:27]2[C:26]([CH3:25])=[CH:31][CH:30]=[CH:29][N:28]=2)[CH2:13][CH2:14]1)([CH3:2])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 1514370(3-Methylpyridin-2-yl)methanamineHCID 5049666Sodium triacetoxyborohydrideHCID 67272519[Tert-butoxycarbonylimino-(4-oxo-piperidin-1-yl)-methyl]-carbamic acid tert-butyl ester

Product 1

HCID 67272689(Tert-butoxycarbonylimino-{4-[(3-methyl-pyridin-2-ylmethyl)-amino]-piperidin-1-yl}-methyl)-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using General Procedure B, reaction of [tert-butoxycarbonylimino-(4-oxo-piperidin-1-yl)-methyl]-carbamic acid tert-butyl ester, C-(3-methylpyridin-2-yl)-methylamine and NaBH(OAc)3 in CH2Cl2 gave (tert-butoxycarbonylimino-{4-[(3-methyl-pyridin-2-ylmethyl)-amino]-piperidin-1-yl}-methyl)-carbamic acid tert-butyl ester as a white solid.

Sources & evidence

ORD record
ord-6e7d27eaf17c4a4781cc11e271ff27b2
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

Loading…