Diisopropylethylamine → 4-Cyclopropylmethyl-1-(4'-fluoro-biphenyl-4-carbonyl)-piperidine-4-carboxylic acid ethyl ester

HRID 2189983Notes

Reaction equation

HRID 2189983 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([OH:16])=O)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.Cl.[CH2:18]([O:20][C:21]([C:23]1([CH2:29][CH:30]2[CH2:32][CH2:31]2)[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)=[O:22])[CH3:19].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[CH2:18]([O:20][C:21]([C:23]1([CH2:29][CH:30]2[CH2:31][CH2:32]2)[CH2:24][CH2:25][N:26]([C:14]([C:11]2[CH:10]=[CH:9][C:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)=[CH:13][CH:12]=2)=[O:16])[CH2:27][CH2:28]1)=[O:22])[CH3:19]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27826894-(4-Fluorophenyl)benzoic acidHCID 131730087HCID 131730087, compound

Product 1

HCID 595279394-Cyclopropylmethyl-1-(4'-fluoro-biphenyl-4-carbonyl)-piperidine-4-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.31 g (1.4 mmol) 4′-fluoro-biphenyl-4-carboxylic acid, 0.426 g (1.71 mmol) 4-cyclopropylmethyl-piperidine-4-carboxylic acid ethyl ester, hydrochloride, 0.552 g (1.71 mmol) TBTU and 1.23 mL DIPEA in 25 mL DMF was stirred at room temperature over night. After evaporation to dryness the residue was purified by column chromatography on silica eluting with a gradient formed from ethyl acetate and heptane to yield after evaporation of the product containing fractions 0.51 g (87%) of the title compound as light yellow viscous oil. MS ISP (m/e): 410.3 [(M+H)+].

Workup

  1. customAfter evaporation to dryness the residue
  2. customwas purified by column chromatography on silica eluting with a gradient
  3. customformed from ethyl acetate and heptane
  4. customto yield
  5. customafter evaporation of the product
  6. additioncontaining fractions 0.51 g (87%) of the title compound as light yellow viscous oil

Sources & evidence

ORD record
ord-0a984c5640c04204afd7a79292a50b43
Source dataset
uspto-grants-2012_12
Patent number
US08324250B2

Reaction notes

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