3-Methylpyridine-2-carboxaldehyde → HCID 67272070, compound

HRID 251039Notes

Reaction equation

[C:1]([O:5][C:6](=[O:12])[NH:7][CH2:8][CH2:9][CH2:10][NH2:11])([CH3:4])([CH3:3])[CH3:2].[CH3:13][C:14]1[C:15]([CH:20]=O)=[N:16][CH:17]=[CH:18][CH:19]=1.[BH-](O[C:32]([CH3:34])=O)(OC(C)=O)OC(C)=O.[Na+]>>[C:1]([O:5][C:6](=[O:12])[NH:7][CH2:8][CH2:9][CH2:10][N:11]([CH2:18][C:17]1[C:32]([CH3:34])=[CH:13][CH:14]=[CH:15][N:16]=1)[CH2:20][C:15]1[C:14]([CH3:13])=[CH:19][CH:18]=[CH:17][N:16]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Reactant 3

HCID 15018743-Methylpyridine-2-carboxaldehyde

HCID 2735700tert-Butyl (3-aminopropyl)carbamate

HCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 67272070HCID 67272070, compoundYield 55%

Procedure

Using General Procedure B: Reaction of (3-aminopropyl)-carbamic acid tert-butyl ester (Houssin, R. et al. Synthesis 1988, 3, 259-261), 3-methylpyridine-2-carboxaldehyde and NaBH(OAc)3 gave {3-[Bis-(3-methyl-pyridin-2-ylmethyl)-amino]-propyl}-carbamic acid tert-butyl ester as a light brown solid (0.17 g, 55%). 1H NMR (CDCl3) δ 1.43 (s, 9H), 1.70 (m, 2H), 2.16 (s, 6H), 2.64 (t, 2H, J=7.5 Hz), 3.02 (m, 2H), 3.74 (s, 4H), 6.02 (br, 1H(NH)), 7.07 (m, 2H), 7.38 (d, 2H, J=6.0 Hz), 8.40 (d, 2H, J=2.8 Hz). Deprotection with TFA following General Procedure F gave N,N-Bis-(3-methyl-pyridin-2-ylmethyl)-propane-1,3-diamine (0.14 g, excess) was isolated, which was used immediately in the next reaction.

Sources & evidence

ORD record: ord-adca87da9f5643dfb0aa8e689b04a8c0
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07863293B2

Reaction notes

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