Diisopropylethylamine → HCID 21902086, compound

HRID 2110308Notes

Reaction equation

HRID 2110308 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:17]=[CH:16][C:6]([O:7][CH2:8][C:9]2([OH:15])[CH2:14][CH2:13][CH2:12][NH:11][CH2:10]2)=[CH:5][CH:4]=1.C(N(C(C)C)CC)(C)C.[Cl:29][C:30]1[CH:35]=[CH:34][C:33]([C:36]2([C:40](O)=[O:41])[CH2:39][CH2:38][CH2:37]2)=[CH:32][CH:31]=1.C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>O.ClCCl>[Cl:29][C:30]1[CH:31]=[CH:32][C:33]([C:36]2([C:40]([N:11]3[CH2:12][CH2:13][CH2:14][C:9]([OH:15])([CH2:8][O:7][C:6]4[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:18])[F:19])=[CH:17][CH:16]=4)[CH2:10]3)=[O:41])[CH2:39][CH2:38][CH2:37]2)=[CH:34][CH:35]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 6027611-(p-Chlorophenyl)cyclobutanecarboxylic acidHCID 2733179PyBroPHCID 21902080HCID 21902080, compound

Product 1

HCID 21902086HCID 21902086, compoundYield 11.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Into a round-bottom flask was added 3-(4-trifluoromethyl-phenoxymethyl)-piperidin-3-ol (100 mg, 0.36 mmol), dichloromethane (5 mL), diisopropylethylamine (0.190 mL, 1.08 mmol), 1-(4-chloro-phenyl)-cyclobutanecarboxylic acid (113.4 mg, 0.54 mmole), and PyBroP (0.252 g, 0.54 mmol). The reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with water and then extracted with ethyl acetate (3×10 mL). The extracts were combined, dried over anhydrous sodium sulfate, filtered, and concentrated to give a yellow oil. The oil was purified by column chromatography on silica gel using hexane/ethyl acetate (4:1) to give [1-(4-Chloro-phenyl)-cyclobutyl]-[3-hydroxy-3-(4-trifluoromethyl-phenoxymethyl)-piperidin-1-yl]-methanone (18.7 mg, 11%). MH+ (468).

Workup

  1. extractionextracted with ethyl acetate (3×10 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a yellow oil
  6. customThe oil was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-da5e914e3f8444bf83d03f3231682c51
Source dataset
uspto-grants-2009_04
Patent number
US07517892B2

Reaction notes

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