Tetrahydrofuran → 4-[5-(4-Methanesulfonyl-phenyl)-2,3-dihydro-benzofuran-2-yl]-piperidine-1-carboxylic acid cyclobutyl ester

HRID 1184727Notes

Reaction equation

HRID 1184727 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[CH:13][C:14]3[O:18][CH:17]([CH:19]4[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]4)[CH2:16][C:15]=3[CH:25]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[C:26](=O)([O-])[O:27]C1C=CC([N+]([O-])=O)=CC=1C1CCC1.C(N(C(C)C)C(C)C)C.[O:52]1[CH2:56][CH2:55][CH2:54][CH2:53]1>>[CH:56]1([O:52][C:26]([N:22]2[CH2:23][CH2:24][CH:19]([CH:17]3[CH2:16][C:15]4[CH:25]=[C:11]([C:8]5[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:10][CH:9]=5)[CH:12]=[CH:13][C:14]=4[O:18]3)[CH2:20][CH2:21]2)=[O:27])[CH2:55][CH2:54][CH2:53]1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 679732894-[5-(4-Methanesulfonylphenyl)-2,3-dihydrobenzofuran-2-yl]piperidineHCID 67973550Cyclobutyl-4-nitrophenyl carbonate

Product 1

HCID 573891384-[5-(4-Methanesulfonyl-phenyl)-2,3-dihydro-benzofuran-2-yl]-piperidine-1-carboxylic acid cyclobutyl ester

Procedure

A mixture of 4-[5-(4-methanesulfonyl-phenyl)-2,3-dihydro-benzofuran-2-yl]-piperidine (100 mg), cyclobutyl-4-nitrophenyl carbonate (67 mg), and ethyldiisopropylamine (46 μL) in tetrahydrofuran (2 mL) is stirred under reflux over night. The solvent is evaporated and the residue is solved in ethyl acetate. The solution is washed with aqueous NaOH solution (1 M) and brine, dried (Na2SO4) and the solvent is evaporated to give the title compound. Yield: 92 mg (72% of theory); LC (method 2): tR=1.45 min; Mass spectrum (ESI+): m/z=456 [M+H]+.

Workup

  1. temperatureunder reflux over night
  2. customThe solvent is evaporated
  3. washThe solution is washed with aqueous NaOH solution (1 M) and brine
  4. dry with materialdried (Na2SO4)
  5. customthe solvent is evaporated

Sources & evidence

ORD record
ord-a0221599894347b6b857f671689c0c83
Source dataset
uspto-grants-2014_03
Patent number
US08669271B2

Reaction notes

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