4-((Tert-butyldimethylsilyl)oxy)aniline → [1-((R)-3-amino-1-methyl-propyl)-piperidin-4-yl]-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-amine

HRID 1726234Notes

Reaction equation

HRID 1726234 reaction equation
[C:1]([Si:5]([CH3:15])([CH3:14])[O:6][C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].O=[C:17]1[CH2:22][CH2:21][N:20]([C@H:23]([CH3:27])[CH2:24][C:25]#[N:26])[CH2:19][CH2:18]1>>[NH2:26][CH2:25][CH2:24][C@H:23]([N:20]1[CH2:21][CH2:22][CH:17]([NH:13][C:10]2[CH:9]=[CH:8][C:7]([O:6][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:15])[CH3:14])=[CH:12][CH:11]=2)[CH2:18][CH2:19]1)[CH3:27]

Participants

3

Reactant 2

HCID 117155534-((Tert-butyldimethylsilyl)oxy)anilineHCID 68972438(betaR)-beta-Methyl-4-oxo-1-piperidinepropanenitrile

Product 1

HCID 68972423[1-((R)-3-amino-1-methyl-propyl)-piperidin-4-yl]-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-amine

Procedure

Using general procedure A with 4-(tert-butyl-dimethyl-silanyloxy)-phenylamine (Swenton, John S.; et al., J. Org. Chem., 54, 1, 1989, 51-58) (1.28 g, 5.73 mmol) and (R)-3-(4-oxo-piperidin-1-yl)-butyronitrile (1.05 g, 6.32 mmol) followed by general procedure J gave [1-((R)-3-amino-1-methyl-propyl)-piperidin-4-yl]-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-amine as a yellow oil (1.81 g, 84% over 2 steps).

Sources & evidence

ORD record
ord-7eac1e63adbe458b92d49c1c6faf3276
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

Loading…