tert-Butyl (3-aminopropyl)carbamate → HCID 67272771, compound

HRID 251222Notes

Reaction equation

HRID 251222 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].[N:13]1[C:22]2[C:21](=O)[CH2:20][CH2:19][CH2:18][C:17]=2[CH:16]=[CH:15][CH:14]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:12])[NH:7][CH2:8][CH2:9][CH2:10][NH:11][CH:21]1[C:22]2[N:13]=[CH:14][CH:15]=[CH:16][C:17]=2[CH2:18][CH2:19][CH2:20]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 2735700tert-Butyl (3-aminopropyl)carbamateHCID 5049666Sodium triacetoxyborohydrideHCID 117447776,7-Dihydro-5H-quinoline-8-one

Product 1

HCID 67272771HCID 67272771, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using General Procedure B, reaction of (3-amino-propyl)-carbamic acid tert-butyl ester, 6,7-dihydro-5H-quinolin-8-one and NaBH(OAc)3 in CH2Cl2 gave [3-(5,6,7,8-tetrahydro-quinolin-8-ylamino)-propyl]-carbamic acid tert-butyl ester as a light brown oil plus ˜15% impurity. 1H NMR (CDCl3) δ 1.43 (s, 9H), 1.77 (m, 4H), 2.00 (m, 2H), 2.80 (m, 4H), 3.24 (m, 2H), 3.74 (t, 1H, J=7.5 Hz), 5.36 (br, 1H(NH)), 7.06 (m, 1H), 7.37 (d, 1H, J=7.5 Hz), 8.39 (d, 1H, J=4.5 Hz).

Sources & evidence

ORD record
ord-2eedc9eb90fb4e8aa8c23cd6d8b8d201
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

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