Tetrahydrofuran → {4-[1-(2,6-Dichloro-benzoyl)-piperidin-4-yloxy]-phenyl}-carbamic acid tert-butyl ester

HRID 499186Notes

Reaction equation

HRID 499186 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][C:8]1[CH:13]=[CH:12]C(O)=C[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[Cl:16][C:17]1[CH:33]=[CH:32][CH:31]=[C:30]([Cl:34])[C:18]=1[C:19](C(N1CCC(O)CC1)=O)=[O:20].C1(P([C:48]2[CH:53]=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:54]([C:61](OCC)=O)=NC(OCC)=O.[CH2:66]1[CH2:70][O:69][CH2:68][CH2:67]1>>[C:1]([O:5][C:6](=[O:15])[NH:7][C:8]1[CH:9]=[CH:66][C:70]([O:69][CH:68]2[CH2:67][CH2:61][N:54]([C:19](=[O:20])[C:18]3[C:30]([Cl:34])=[CH:31][CH:32]=[CH:33][C:17]=3[Cl:16])[CH2:53][CH2:48]2)=[CH:12][CH:13]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 5

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2756771N-Boc-4-hydroxyanilineHCID 23103416(2,6-Dichlorobenzoyl)-(4-hydroxy-piperidin-1-yl)-methanone

Product 1

HCID 59420870{4-[1-(2,6-Dichloro-benzoyl)-piperidin-4-yloxy]-phenyl}-carbamic acid tert-butyl esterYield 64.8%

Conditions

Temperature
22 °C

Procedure

To an ice-cooled solution of (4-hydroxy-phenyl)-carbamic acid tert-butyl ester (422.8 mg, 2.02 mmol), (2,6-dichlorobenzoyl)-(4-hydroxy-piperidin-1-yl)-methanone (552.8 mg, 2.01 mmol), and triphenylphosphine (1.09 g, 4.16 mmol) in THF (20 mL) is added diethyl azodicarboxylate (1.0 mL, 2.20 mmol). The reaction mixture is stirred at 22° C. for 17 hours. After removal of solvent, the residue is purified on a silica gel chromatography with ethyl acetate-hexanes to provide a white solid (606.2 mg, 64.8% yield, ES+(m/z) 465.1 [M+H]).

Workup

  1. customAfter removal of solvent
  2. customthe residue is purified on a silica gel chromatography with ethyl acetate-hexanes
  3. customto provide a white solid (606.2 mg, 64.8% yield, ES+(m/z) 465.1 [M+H])

Sources & evidence

ORD record
ord-0a8e7bb364d041e18c268b5b72a436e4
Source dataset
uspto-grants-2010_08
Patent number
US07767674B2

Reaction notes

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