Sodium triacetoxyborohydride → [4-(Tert-butyl-dimethyl-silanyloxy)-butyl]-(3,5-dimethyl-pyridin-2-yl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine

HRID 251227Notes

Reaction equation

HRID 251227 reaction equation
[CH3:1][C:2]1[C:3]([NH:9][CH:10]2[C:19]3[N:18]=[CH:17][CH:16]=[CH:15][C:14]=3[CH2:13][CH2:12][CH2:11]2)=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1.[C:20]([Si:24]([CH3:32])([CH3:31])[O:25][CH2:26][CH2:27][CH2:28][CH:29]=O)([CH3:23])([CH3:22])[CH3:21].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[C:20]([Si:24]([CH3:31])([CH3:32])[O:25][CH2:26][CH2:27][CH2:28][CH2:29][N:9]([C:3]1[C:2]([CH3:1])=[CH:7][C:6]([CH3:8])=[CH:5][N:4]=1)[CH:10]1[C:19]2[N:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH2:13][CH2:12][CH2:11]1)([CH3:23])([CH3:22])[CH3:21]

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 108889764-((Tert-butyldimethylsilyl)oxy)butanalHCID 67273035(3,5-Dimethyl-pyridin-2-yl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine

Product 1

HCID 67271684[4-(Tert-butyl-dimethyl-silanyloxy)-butyl]-(3,5-dimethyl-pyridin-2-yl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using General Procedure B, reaction of (3,5-dimethyl-pyridin-2-yl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine, 4-(tert-butyl-dimethyl-silanyloxy)-butyraldehyde and NaBH(OAc)3 in CH2Cl2 gave [4-(tert-butyl-dimethyl-silanyloxy)-butyl]-(3,5-dimethyl-pyridin-2-yl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine.

Sources & evidence

ORD record
ord-63159ee2bf454175a82a243e9b4ef922
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

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