Sodium triacetoxyborohydride → HCID 67272021, compound

HRID 251291Notes

Reaction equation

HRID 251291 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[CH2:11][NH:12][CH:13]1[C:22]2[N:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH2:16][CH2:15][CH2:14]1)[C:6]#[N:7].[C:23]([C:27]1[CH:32]=[CH:31][N:30]=[C:29]([CH:33]=O)[CH:28]=1)([CH3:26])([CH3:25])[CH3:24].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[C:23]([C:27]1[CH:32]=[CH:31][N:30]=[C:29]([CH2:33][N:12]([CH2:11][C:10]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=2[CH2:2][OH:1])[CH:13]2[C:22]3[N:21]=[CH:20][CH:19]=[CH:18][C:17]=3[CH2:16][CH2:15][CH2:14]2)[CH:28]=1)([CH3:26])([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 187996954-(tert-butyl)picolinaldehydeHCID 67271659HCID 67271659, compound

Product 1

HCID 67272021HCID 67272021, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using General Procedure B: Reaction of 3-hydroxymethyl-4-[(5,6,7,8-tetrahydro-quinolin-8-ylamino)-methyl]-benzonitrile in CH2Cl2 with 4-tert-butyl-pyridine-2-carbaldehyde and NaBH(OAc)3 gave 4-{[(4-tert-butyl-pyridin-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-3-hydroxymethyl-benzonitrile as a pale yellow oil. 1H NMR (CDCl3) δ 1.38 (s, 9H), 1.70 (m, 1H), 1.91-2.04 (m, 2H), 2.21 (m, 1H), 2.71 (m, 1H), 2.81 (m, 1H), 3.52 (d, 1H, J=12.0 Hz), 3.64 (d, 1H, J=12.0 Hz), 3.73 (d, 1H, J=12.0 Hz), 3.80 (m, 1H), 4.07 (m, 1H), 4.13 (d, 1H, J=12.0 Hz), 4.34 (d, 1H, J=12.0 Hz), 7.03 (dd, 1H, J=7.5, 3.0 Hz), 7.19 (dd, 1H, J=4.5, 3.0 Hz), 7.36-7.52 (m, 4H), 7.63 (s, 1H), 7.78 (s, 1H), 8.36 (d, 1H, J=6.0 Hz), 8.51 (d, 1H, J=3.0 Hz).

Sources & evidence

ORD record
ord-4ea60ada4f914b6dac04a9aa10cc9a78
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

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