Ethyl Acetate → HCID 68811023, compound

HRID 434291Notes

Reaction equation

HRID 434291 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[O:9])=[CH:4][CH:3]=1.[C:16]([O:20][C:21](=[O:33])[NH:22][C@H:23]([CH2:26][C:27]1[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=1)[CH2:24]Br)([CH3:19])([CH3:18])[CH3:17].N12CCCN=C1CCCCC2.C(OC(=O)C)C>CN(C)C=O.O>[C:16]([O:20][C:21](=[O:33])[NH:22][C@H:23]([CH2:26][C:27]1[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=1)[CH2:24][N:13]1[CH2:14][CH2:15][CH:10]([C:8](=[O:9])[C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[CH2:11][CH2:12]1)([CH3:17])([CH3:18])[CH3:19]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 27244404-(4-Fluorobenzoyl)piperidineHCID 68809313HCID 68809313, compound

Product 1

HCID 68811023HCID 68811023, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

(4-Fluoro-phenyl)-piperidin-4-yl-methanone (0.15 g, 0.73 mmol) is added to a solution of ((R)-2-Bromo-1-pyridin-3-ylmethyl-ethyl)-carbamic acid tert-butyl ester (0.21 g, 0.66 mmol) and 1,8 diazabicyclo[5.4.0]undec-7-ene (0.12 ml, 0.79 mmol) in dimethylformamide (3 ml). The reaction mixture is stirred at ambient temperature for 24 hours prior to partioning between ethylacetate and water. The ethylacetate is dried over magnesium sulphate and evaporated. The crude product is purified by flash silica chromatography (97:3 dichloromethane: methanol elution) to afford {(R)-2-[4-(4-fluoro-benzoyl)-piperidin-1-yl]-1-pyridin-3-ylmethyl-ethyl}-carbamic acid tert-butyl ester. 1H NMR (400 MHz, CDCl3) δ 1.36 (s, 9H), 1.68-1.85 (br m, 4H), 2.00-2.38 (br m, 4H), 2.78-2.91 (m, 4H), 3.05-3.19 (m 1H), 3.81-3.93 (m 1H) 7.05 (t J 8.8 2H), 7.12-7.18 (m 1H), 7.48 (d J 7.9 1H), 7.85-7.93 (dd J 8.8 5.4 2H), 8.36 (d J 1.5 1H), 8.40 (dd J 4.9 1.5 1H).

Workup

  1. dry with materialThe ethylacetate is dried over magnesium sulphate
  2. customevaporated
  3. customThe crude product is purified by flash silica chromatography (97:3 dichloromethane: methanol elution)

Sources & evidence

ORD record
ord-0a00758477ea44a18aa2e9dccff7114f
Source dataset
uspto-grants-2003_12
Patent number
US06670379B2

Reaction notes

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