Sodium triacetoxyborohydride → HCID 67271972, compound

HRID 251224Notes

Reaction equation

HRID 251224 reaction equation
[C:1]([O:5][C:6](=[O:22])[NH:7][CH2:8][CH2:9][CH2:10][NH:11][CH:12]1[C:21]2[N:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH2:15][CH2:14][CH2:13]1)([CH3:4])([CH3:3])[CH3:2].[CH3:23][C:24]1[C:25](C=O)=[N:26][CH:27]=[C:28]([CH3:30])[CH:29]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:22])[NH:7][CH2:8][CH2:9][CH2:10][N:11]([C:25]1[C:24]([CH3:23])=[CH:29][C:28]([CH3:30])=[CH:27][N:26]=1)[CH:12]1[C:21]2[N:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH2:15][CH2:14][CH2:13]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 187316833,5-Dimethylpyridine-2-carbaldehydeHCID 67272771HCID 67272771, compound

Product 1

HCID 67271972HCID 67271972, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using General Procedure B, reaction of [3-(5,6,7,8-tetrahydro-quinolin-8-ylamino)-propyl]-carbamic acid tert-butyl ester, 3,5-dimethylpyridine-2-carboxaldehyde and NaBH(OAc)3 in CH2Cl2 gave {3-[(3,5-dimethyl-pyridin-2-yl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-propyl}-carbamic acid tert-butyl ester as a pale beige sticky solid. 1H NMR (CDCl3) δ 1.75 (m, 4H), 2.18 (br t, 1H), 2.27 (s, 3H), 2.30 (s, 3H), 2.37 (br, 1H), 2.56 (t, 1H, J=10.5 Hz), 2.83 (m, 4H), 3.38 (br, 1H), 3.68 (d, 1H, J=15.0 Hz), 3.84 (br, 1H), 4.04 (d, 1H, J=15.0 Hz), 7.13 (m, 1H), 7.26 (s, 1H), 7.41 (d, 1H, J=7.0 Hz), 8.33 (s, 1H), 8.53 (d, 1H, J=4.5 Hz). Deprotection with TFA using General Procedure F gave N′-(3,5-dimethyl-pyridin-2-yl)-N′-(5,6,7,8-tetrahydro-quinolin-8-yl)-propane-1,3-diamine as a white solid.

Sources & evidence

ORD record
ord-28c0bd5395974f1999747521136ad794
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

Loading…