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

HRID 1592374Notes

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].[CH:14]([C:17]1[C:18]([CH:23]=O)=[N:19][CH:20]=[CH:21][CH:22]=1)([CH3:16])[CH3:15]>>[C:1]([O:5][C:6](=[O:13])[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][NH:12][CH2:23][C:18]1[C:17]([CH:14]([CH3:16])[CH3:15])=[CH:22][CH:21]=[CH:20][N:19]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Reactant 2

HCID 4351tert-butyl N-(4-aminobutyl)carbamate

HCID 450836353-Isopropylpicolinaldehyde

Product 1

HCID 58997088{4-[(3-Isopropyl-pyridin-2-ylmethyl)-amino]-butyl}-carbamic acid tert-butyl ester

Procedure

A pale yellow oil prepared from (4-amino-butyl)-carbamic acid tert-butyl ester and 3-isopropyl-pyridine-2-carbaldehyde. 1H NMR (CDCl3) δ 1.23 (d, 6H, J=6.6 Hz), 1.43 (s, 9H), 1.53-1.61 (m, 4H), 2.67-2.74 (m, 2H), 3.10-3.21 (m, 3H), 3.94 (s, 2H), 4.73 (s, br. 1H), 7.11-7.17 (m, 1H), 7.54-7.58 (m, 1H), 8.37-7.40 (m, 1H).

Sources & evidence

ORD record: ord-87e2d36c3e8f4a87b10af780e400e403
Source dataset: uspto-grants-2007_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07291631B2

Reaction notes

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