4-(N-Ethylaminocarbonyl)phenylboronic acid → 5-(4-Ethylaminocarbonyl-phenyl)-1''-tert-butoxycarbonyl-dispiro[2,3-dihydrofuro[2,3-c]pyridine-2,1'-cyclobutane-3',4''-piperidine]

HRID 2406356

Reaction equation

HRID 2406356 reaction equation
Cl[C:2]1[CH:3]=[C:4]2[CH2:25][C:9]3([CH2:24][C:11]4([CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]4)[CH2:10]3)[O:8][C:5]2=[CH:6][N:7]=1.[CH2:26]([NH:28][C:29]([C:31]1[CH:36]=[CH:35][C:34](B(O)O)=[CH:33][CH:32]=1)=[O:30])[CH3:27]>>[CH2:26]([NH:28][C:29]([C:31]1[CH:36]=[CH:35][C:34]([C:2]2[CH:3]=[C:4]3[CH2:25][C:9]4([CH2:24][C:11]5([CH2:12][CH2:13][N:14]([C:17]([O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:18])[CH2:15][CH2:16]5)[CH2:10]4)[O:8][C:5]3=[CH:6][N:7]=2)=[CH:33][CH:32]=1)=[O:30])[CH3:27]

Participants

3

Reactant 2

HCID 34113074-(N-Ethylaminocarbonyl)phenylboronic acidHCID 86701200HCID 86701200, compound

Product 1

HCID 721949795-(4-Ethylaminocarbonyl-phenyl)-1''-tert-butoxycarbonyl-dispiro[2,3-dihydrofuro[2,3-c]pyridine-2,1'-cyclobutane-3',4''-piperidine]

Procedure

The title compound is prepared from 5-chloro-1″-tert-butoxycarbonyl-dispiro[2,3-dihydrofuro[2,3-c]pyridine-2,1′-cyclobutane-3′,4″-piperidine] and 4-ethylaminocarbonyl-phenylboronic acid following a procedure analogous to that described for Example 1; the reaction is conducted in a microwave oven at 140° C. LC (method 3): tR=1.26 min; Mass spectrum (ESI+): m/z=478 [M+H]+.

Workup

  1. customthe reaction is conducted in a microwave oven at 140° C

Sources & evidence

ORD record
ord-2a1fc7c365b14d7a9e4c03fd5b333be1
Source dataset
uspto-grants-2014_08
Patent number
US08809361B2

Linked notes

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