Tert-butyl [2-(4-fluorophenyl)-4-(3-thiomorpholin-4-ylazetidin-1-yl)butyl]methylcarbamate → 1-{1-[(3S)-3-(3,4-Dichlorophenyl)-4-(methylamino)butyl]azetidin-3-yl]piperidin-4-ol dihydrochloride

HRID 749429Notes

Reaction equation

HRID 749429 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]([CH2:20][CH2:21][N:22]2[CH2:25][CH:24]([N:26]3[CH2:31][CH2:30][CH:29]([OH:32])[CH2:28][CH2:27]3)[CH2:23]2)[CH2:10][N:11](C)[C:12](=O)OC(C)(C)C)[CH:5]=[CH:6][C:7]=1[Cl:8].FC1C=CC(C(CCN2CC(N3CCSCC3)C2)CN(C)C(=O)OC(C)(C)C)=CC=1>>[ClH:1].[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:9]([CH2:10][NH:11][CH3:12])[CH2:20][CH2:21][N:22]2[CH2:25][CH:24]([N:26]3[CH2:31][CH2:30][CH:29]([OH:32])[CH2:28][CH2:27]3)[CH2:23]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

3

Reactant 2

HCID 86606882Tert-butyl [2-(4-fluorophenyl)-4-(3-thiomorpholin-4-ylazetidin-1-yl)butyl]methylcarbamateHCID 86606883tert-Butyl {(2S)-2-(3,4-dichlorophenyl)-4-[3-(4-hydroxypiperidin-1-yl)azetidin-1-yl]butyl}methylcarbamate

Product 1

HCID 689767921-{1-[(3S)-3-(3,4-Dichlorophenyl)-4-(methylamino)butyl]azetidin-3-yl]piperidin-4-ol dihydrochloride

Procedure

The compound was synthesized in an analogous way to that of Method 3e but using tert-butyl {(2S)-2-(3,4-dichlorophenyl)-4-[3-(4-hydroxypiperidin-1-yl)azetidin-1-yl]butyl}methylcarbamate rather than tert-butyl [2-(4-fluorophenyl)-4-(3-thiomorpholin-4-ylazetidin-1-yl)butyl]methylcarbamate (yield, 100%). 1H NMR (500 MHz, CD3OD): 1.8-2.2 (m, 6H), 2.7 (s, 3H), 3.2-4.8 (cm, 17H), 7.4 (dd, 1H), 7.6-7.7 (m, 2H), LCMS: m/z 387 (M+1)+.

Workup

  1. customThe compound was synthesized in an analogous way to that of Method 3e

Sources & evidence

ORD record
ord-662adb1d7088431e87bd54bfe6a9c8d4
Source dataset
uspto-grants-2008_07
Patent number
US07402581B2

Reaction notes

Loading…