(3-Methylpyridin-2-yl)methanamine → (2-{[(3-Methyl-pyridin-2-ylmethyl)-amino]-methyl}-pyridin-3-yl)-carbamic acid tert-butyl ester

HRID 251236Notes

Reaction equation

HRID 251236 reaction equation
[CH3:1][C:2]1[C:3]([CH2:8][NH2:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[C:10]([O:14][C:15](=[O:25])[NH:16][C:17]1[C:18]([CH:23]=O)=[N:19][CH:20]=[CH:21][CH:22]=1)([CH3:13])([CH3:12])[CH3:11].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[C:10]([O:14][C:15](=[O:25])[NH:16][C:17]1[C:18]([CH2:23][NH:9][CH2:8][C:3]2[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][N:4]=2)=[N:19][CH:20]=[CH:21][CH:22]=1)([CH3:13])([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 1514370(3-Methylpyridin-2-yl)methanamineHCID 5049666Sodium triacetoxyborohydrideHCID 10911130tert-butyl N-(2-formylpyridin-3-yl)carbamate

Product 1

HCID 67271562(2-{[(3-Methyl-pyridin-2-ylmethyl)-amino]-methyl}-pyridin-3-yl)-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using General Procedure B: Reaction of C-(3-methyl-pyridin-2-yl)-methylamine and (2-formyl-pyridin-3-yl)-carbamic acid tert-butyl ester with NaBH(OAc)3 in CH2Cl2 gave (2-{[(3-Methyl-pyridin-2-ylmethyl)-amino]-methyl}-pyridin-3-yl)-carbamic acid tert-butyl ester as a yellow oil.

Sources & evidence

ORD record
ord-753c048c04614bf48d700fe6100bc106
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

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