tert-butyl N-(4-aminobutyl)carbamate → HCID 67272418, compound

HRID 251086Notes

Reaction equation

HRID 251086 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[CH:7]=O.[C:9]([O:13][C:14](=[O:21])[NH:15][CH2:16][CH2:17][CH2:18][CH2:19][NH2:20])([CH3:12])([CH3:11])[CH3:10]>C(Cl)Cl.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>[C:9]([O:13][C:14](=[O:21])[NH:15][CH2:16][CH2:17][CH2:18][CH2:19][NH:20][CH2:7][C:3]1[N:2]([CH3:1])[CH:6]=[CH:5][N:4]=1)([CH3:12])([CH3:10])[CH3:11]

Participants

5

Reactant 2

HCID 4351tert-butyl N-(4-aminobutyl)carbamateHCID 1395751-Methyl-2-imidazolecarboxaldehyde

Product 1

HCID 67272418HCID 67272418, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 5049666Sodium triacetoxyborohydrideSolvent

Procedure

Using General Procedure B, reaction of 1-methyl-1H-imidazole-2-carbaldehyde and (4-amino-butyl)-carbamic acid tert-butyl ester in CH2Cl2 and NaBH(OAc)3 gave {4-[(1-methyl-1H-imidazol-2-ylmethyl)-amino]-butyl}-carbamic acid tert-butyl ester as a sticky white foam. 1H NMR (CDCl3) δ 1.43 (s, 9H), 1.50-1.59 (m, 4H), 2.01 (s, 3H), 2.04-2.06 (m, 2H), 2.62-2.73 (m, 2H), 3.08-3.17 (m, 2H), 3.79 (s, 2H), 6.85 (d, 1H, J=2.2 Hz), 7.11 (d, 1H, J=1.8 Hz).

Sources & evidence

ORD record
ord-edb34e2f6f26457bbf5f9d537c0276d9
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

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