tert-butyl N-(4-aminobutyl)carbamate → {4-[(5-Chloro-3-methyl-pyridin-2-ylmethyl)-amino]-butyl}-carbamic acid tert-butyl ester

HRID 251050Notes

Reaction equation

HRID 251050 reaction equation
[C:1]([O:5][C:6](=[O:13])[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][NH2:12])([CH3:4])([CH3:3])[CH3:2].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[Cl:28][C:29]1[CH:30]=[C:31]([CH3:37])[C:32]([CH:35]=O)=[N:33][CH:34]=1>C(Cl)Cl>[C:1]([O:5][C:6](=[O:13])[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][NH:12][CH2:35][C:32]1[C:31]([CH3:37])=[CH:30][C:29]([Cl:28])=[CH:34][N:33]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 4351tert-butyl N-(4-aminobutyl)carbamateHCID 5049666Sodium triacetoxyborohydrideHCID 722140555-Chloro-3-methylpicolinaldehyde

Product 1

HCID 67272212{4-[(5-Chloro-3-methyl-pyridin-2-ylmethyl)-amino]-butyl}-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using General Procedure B: Reaction of (4-amino-butyl)-carbamic acid tert-butyl ester in CH2Cl2 and 5-chloro-3-methyl-pyridine-2-carbaldehyde with NaBH(OAc)3 gave {4-[(5-chloro-3-methyl-pyridin-2-ylmethyl)-amino]-butyl}-carbamic acid tert-butyl ester as a colorless oil. 1H NMR (CDCl3) δ 1.41 (s, 9H), 1.54 (m, 4H), 2.13 (s, 1H), 2.28 (s, 3H), 2.68 (t, 2H, J=6.0 Hz), 3.11 (d, 2H, J=6.0 Hz), 3.81 (s, 2H), 4.77 (br s, 1H), 7.41 (s, 1H), 8.31 (s, 1H).

Sources & evidence

ORD record
ord-08fc0d0daa934a249f0f7110b4b583a7
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

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