N-(4-Aminobutyl)-N-methyl carbamic acid tert-butyl ester → HCID 67272079, compound

HRID 1592627Notes

Reaction equation

HRID 1592627 reaction equation
[N:1]1[C:10]2[C:9](=O)[CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:12]([O:16][C:17](=[O:25])[N:18]([CH2:20][CH2:21][CH2:22][CH2:23][NH2:24])[CH3:19])([CH3:15])([CH3:14])[CH3:13].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[C:12]([O:16][C:17](=[O:25])[N:18]([CH3:19])[CH2:20][CH2:21][CH2:22][CH2:23][NH:24][CH:9]1[C:10]2[N:1]=[CH:2][CH:3]=[CH:4][C:5]=2[CH2:6][CH2:7][CH2:8]1)([CH3:15])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 2756377N-(4-Aminobutyl)-N-methyl carbamic acid tert-butyl esterHCID 5049666Sodium triacetoxyborohydrideHCID 117447776,7-Dihydro-5H-quinoline-8-one

Product 1

HCID 67272079HCID 67272079, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using General Procedure B: Reaction of 6,7-dihydro-5H-quinolin-8-one, (4-amino-butyl)-methyl-carbamic acid tert-butyl ester and NaBH(OAc)3 in CH2Cl2 gave methyl-[4-(5,6,7,8-tetrahydro-quinolin-8-ylamino)-butyl]-carbamic acid tert-butyl ester as a yellow oil. 1H NMR (CDCl3) δ 1.45 (s, 9H), 1.50-1.60 (m, 4H), 1.72-1.81 (m, 2H), 1.95-2.20 (m, 4H), 2.67-2.78 (m, 4H), 2.83 (s, 3H), 3.17-3.24 (m, 2H), 3.75-3.79 (m, 1H), 7.06 (dd, 1H, J=7.6, 4.7 Hz), 7.36 (d, 1H, J=7.7 Hz), 8.38 (d, 1H, J=4.5 Hz).

Sources & evidence

ORD record
ord-446ebe861548491cb5c1b535183ebdaf
Source dataset
uspto-grants-2007_11
Patent number
US07291631B2

Reaction notes

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