Sodium triacetoxyborohydride → (S)-(3,5-dimethyl-pyridin-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine

HRID 251273Notes

Reaction equation

HRID 251273 reaction equation
[N:1]1[C:10]2[C@@H:9]([NH2:11])[CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH3:12][C:13]1[C:14]([CH:20]=O)=[N:15][CH:16]=[C:17]([CH3:19])[CH:18]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[CH3:12][C:13]1[C:14]([CH2:20][NH:11][C@@H:9]2[C:10]3[N:1]=[CH:2][CH:3]=[CH:4][C:5]=3[CH2:6][CH2:7][CH2:8]2)=[N:15][CH:16]=[C:17]([CH3:19])[CH:18]=1

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 12031071(8S)-5,6,7,8-Tetrahydroquinolin-8-amineHCID 187316833,5-Dimethylpyridine-2-carbaldehyde

Product 1

HCID 67272067(S)-(3,5-dimethyl-pyridin-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using General Procedure B: Reaction of (S)-5,6,7,8-tetrahydro-quinolin-8-ylamine in CH2Cl2 with 3,5-dimethyl-pyridine-2-carbaldehyde and NaBH(OAc)3 gave (S)-(3,5-dimethyl-pyridin-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine. 1H NMR (CDCl3) δ 1.75 (m, 1H), 1.91 (m, 2H), 2.26 (s+m, 4H), 2.33 (s, 3H), 2.80 (m, 2H), 3.96 (t, 1H, J=6.0 Hz), 4.02 (d, 1H, J=15.0 Hz), 4.17 (d, 1H, J=15.0 Hz), 5.41 (br s, 1H), 7.06 (dd, 1H, J=7.5, 3.0 Hz), 7.25 (s, 1H), 7.37 (d, 1H, J=9.0 Hz), 8.24 (s, 1H), 8.40 (d, 1H, J=3.0 Hz).

Sources & evidence

ORD record
ord-9b1fe252150d49d7ba11aa8ecaef808c
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

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