tert-Butyl [(2S)-2-(3,4-dichlorophenyl)-4-oxobutyl]methylcarbamate → tert-Butyl {(2S)-2-(3,4-dichlorophenyl)-4-[3-(4-hydroxypiperidin-1-yl)azetidin-1-yl]butyl}methylcarbamate

HRID 749428Notes

Reaction equation

HRID 749428 reaction equation
Cl.Cl.[NH:3]1[CH2:6][CH:5]([N:7]2[CH2:12][CH2:11][CH:10]([OH:13])[CH2:9][CH2:8]2)[CH2:4]1.[Cl:14][C:15]1[CH:16]=[C:17]([C@H:22]([CH2:33][CH:34]=O)[CH2:23][N:24]([CH3:32])[C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH:18]=[CH:19][C:20]=1[Cl:21].Cl.Cl.N1CC(N2CCSCC2)C1.FC1C=CC(C(CC=O)CN(C)C(=O)OC(C)(C)C)=CC=1>>[Cl:14][C:15]1[CH:16]=[C:17]([C@H:22]([CH2:33][CH2:34][N:3]2[CH2:6][CH:5]([N:7]3[CH2:12][CH2:11][CH:10]([OH:13])[CH2:9][CH2:8]3)[CH2:4]2)[CH2:23][N:24]([CH3:32])[C:25](=[O:31])[O:26][C:27]([CH3:29])([CH3:30])[CH3:28])[CH:18]=[CH:19][C:20]=1[Cl:21]

Participants

5

Reactant 4

HCID 15433413tert-Butyl [(2S)-2-(3,4-dichlorophenyl)-4-oxobutyl]methylcarbamateHCID 457899201-(3-Azetidinyl)-4-piperidinol dihydrochlorideHCID 689763864-Azetidin-3-ylthiomorpholine dihydrochlorideHCID 86606881Tert-butyl [2-(4-fluorophenyl)-4-oxobutyl]methylcarbamate

Product 1

HCID 86606883tert-Butyl {(2S)-2-(3,4-dichlorophenyl)-4-[3-(4-hydroxypiperidin-1-yl)azetidin-1-yl]butyl}methylcarbamate

Procedure

The compound was synthesized in an analogous way to that of Method 3d but using 1-azetidin-3-ylpiperidin-4-ol dihydrochloride (see Meth 15) and tert-butyl [(2S)-2-(3,4-dichlorophenyl)-4-oxobutyl]methylcarbamate (see WO 95/05377) rather than 4-azetidin-3-ylthiomorpholine dihydrochloride and tert-butyl [2-(4-fluorophenyl)-4-oxobutyl]methylcarbamate (yield, 35%). 1H NMR (500 MHz, CDCl3): 1.3 (m, 2H), 1.4 (s, 9H), 1.5-3.8 (cm, 23H), 7.0 (dd, 1H), 7.2-7.4 (m, 2H), LCMS: m/z 487 (M+1)+.

Workup

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

Sources & evidence

ORD record
ord-69de515fe78c46f283688f62002f66b3
Source dataset
uspto-grants-2008_07
Patent number
US07402581B2

Reaction notes

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