Sodium triacetoxyborohydride → {2-[(5,6,7,8-Tetrahydro-quinolin-8-ylamino)-methyl]-pyridin-3-yl}-carbamic acid tert-butyl ester

HRID 251269Notes

Reaction equation

HRID 251269 reaction equation
[N:1]1[C:10]2[CH:9]([NH2:11])[CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:12]([O:16][C:17](=[O:27])[NH:18][C:19]1[C:20]([CH:25]=O)=[N:21][CH:22]=[CH:23][CH:24]=1)([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:27])[NH:18][C:19]1[C:20]([CH2:25][NH:11][CH:9]2[C:10]3[N:1]=[CH:2][CH:3]=[CH:4][C:5]=3[CH2:6][CH2:7][CH2:8]2)=[N:21][CH:22]=[CH:23][CH:24]=1)([CH3:15])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 10911130tert-butyl N-(2-formylpyridin-3-yl)carbamateHCID 113555648-Amino-5,6,7,8-tetrahydroquinoline

Product 1

HCID 67272260{2-[(5,6,7,8-Tetrahydro-quinolin-8-ylamino)-methyl]-pyridin-3-yl}-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using General Procedure B: Reaction of 5,6,7,8-tetrahydro-quinolin-8-ylamine in CH2Cl2 with (2-formyl-pyridin-3-yl)-carbamic acid tert-butyl ester and NaBH(OAc)3 gave {2-[(5,6,7,8-tetrahydro-quinolin-8-ylamino)-methyl]-pyridin-3-yl}-carbamic acid tert-butyl ester as a yellow oil. 1H NMR (CDCl3) δ 1.51 (s, 9H), 1.85-1.94 (m, 2H), 1.98-2.08 (m, 2H), 2.78-2.84 (m, 2H), 3.82-3.86 (m, 1H), 4.19 (s, 2H), 7.11-7.19 (m, 2H), 7.42 (d, 1H, J=7.1 Hz), 8.15-8.17 (m, 1H), 8.28 (d, 1H, J=8.0 Hz), 8.44 (d, 1H, J=3.0 Hz), 10.17 (s, 1H).

Sources & evidence

ORD record
ord-a3fcb347bb324a80aa59418327d914b9
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

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