Sodium triacetoxyborohydride → 2-{4-[[3-(tert-Butyldimethylsilanyloxymethyl)-pyridin-2-ylmethyl]-(5,6,7,8-tetrahydroquinolin-8-yl)-amino]-butyl}-isoindole-1,3-dione

HRID 251202Notes

Reaction equation

HRID 251202 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[C:11]([CH:16]=O)=[N:12][CH:13]=[CH:14][CH:15]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[N:18]1[C:27]2[CH:26]([NH:28][CH2:29][CH2:30][CH2:31][CH2:32][N:33]3[C:41](=[O:42])[C:40]4[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=4)[C:34]3=[O:43])[CH2:25][CH2:24][CH2:23][C:22]=2[CH:21]=[CH:20][CH:19]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[Si:1]([O:8][CH2:9][C:10]1[C:11]([CH2:16][N:28]([CH:26]2[C:27]3[N:18]=[CH:19][CH:20]=[CH:21][C:22]=3[CH2:23][CH2:24][CH2:25]2)[CH2:29][CH2:30][CH2:31][CH2:32][N:33]2[C:34](=[O:43])[C:35]3[C:40](=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:41]2=[O:42])=[N:12][CH:13]=[CH:14][CH:15]=1)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 589971372-[4-(5,6,7,8-Tetrahydroquinolin-8-ylamino)-butyl]-isoindole-1,3-dioneHCID 873329733-(Tert-butyl-dimethylsiloxymethyl)-pyridine-2-carbaldehyde

Product 1

HCID 672721812-{4-[[3-(tert-Butyldimethylsilanyloxymethyl)-pyridin-2-ylmethyl]-(5,6,7,8-tetrahydroquinolin-8-yl)-amino]-butyl}-isoindole-1,3-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using General Procedure B, reaction of 3-(tert-Butyldimethylsilanyloxymethyl)-pyridine-2-carbaldehyde, 2-[4-(5,6,7,8-Tetrahydroquinolin-8-ylamino)-butyl]-isoindole-1,3-dione and NaBH(OAc)3 in CH2Cl2 gave 2-{4-[[3-(tert-Butyldimethylsilanyloxymethyl)-pyridin-2-ylmethyl]-(5,6,7,8-tetrahydroquinolin-8-yl)-amino]-butyl}-isoindole-1,3-dione as a light brown solid. 1H NMR (CDCl3) δ 0.11 (s, 6H), 0.95 (s, 9H), 1.31 (m, 2H), 1.49 (quintet, 2H, J=7.5 Hz), 1.59 (m, 1H), 1.85-2.08 (m, 3H), 2.47 (m, 1H), 2.59 (m, 2H), 2.67 (m, 1H), 3.49 (t, 2H, J=7.5 Hz), 3.90 (m, 1H), 3.96 (d, 1H, J=12.0 Hz), 4.11 (d, 1H, J=12.0 Hz), 4.98 (d, 1H, J=15.0 Hz), 5.20 (d, 1H, J=15.0 Hz), 6.99 (m, 1H), 7.13 (m, 1H), 7.28 (d, 1H, J=7.5 Hz), 7.68 (m, 2H), 7.80 (m, 2H), 7.82 (d, 1H, J=7.5 Hz), 8.32 (d, 1H, J=3.0 Hz), 8.42 (d, 1H, J=3.0 Hz).

Sources & evidence

ORD record
ord-ca1b671364ce4eabbdd245396c315153
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

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