Acetic Acid → HCID 59376115, compound

HRID 2093738Notes

Reaction equation

HRID 2093738 reaction equation
[CH2:1]([O:3][C:4]([C@H:6]1[CH2:11][CH2:10][CH2:9][N:8]([C:12](=[O:20])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH3:19])[C@H:7]1[C:21]1[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][CH:22]=1)=[O:5])[CH3:2].[C:28]1(=O)[CH2:32][CH2:31][CH2:30][CH2:29]1.C(O)(=O)C>ClC(Cl)C.C(Cl)Cl>[CH2:1]([O:3][C:4]([C@H:6]1[CH2:11][CH2:10][CH2:9][N:8]([C:12](=[O:20])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH3:19])[C@H:7]1[C:21]1[CH:22]=[CH:23][C:24]([NH:27][CH:28]2[CH2:32][CH2:31][CH2:30][CH2:29]2)=[CH:25][CH:26]=1)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 8452CyclopentanoneHCID 59376139HCID 59376139, compound

Product 1

HCID 59376115HCID 59376115, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
50 °C

Procedure

Na(OAC)3BH (495 mg, 2.33 mmol) was added to a solution of the (2R,3S)-2-(4-aminophenyl)-1-(2-methylbenzoyl)piperidine-3-carboxylic acid ethyl ester (612 mg, 1.67 mmol), cyclopentanone (140 mg, 1.67 mmol) and acetic acid (100 mg, 1.67 mmol) in dry dichloroethane at r.t and the reaction mixture was heated to 50° C. for 4 h, cooled to r.t and stirred for 48 h. It was then diluted with CH2Cl2 (30 mL), washed with saturated aqueous NaHCO3 solution, dried and concentrated in vacuo. The residue was purified by ISCO flash column using ethyl acete and hexanes as mobile phase (40 g column, 0-40% gradient) to afford (2R,3S)-2-(4-Cyclopentylaminophenyl)-1-(2-methylbenzoyl)piperidine-3-carboxylic acid ethyl ester (450 mg).

Workup

  1. temperaturecooled
  2. washwashed with saturated aqueous NaHCO3 solution
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by ISCO flash column

Sources & evidence

ORD record
ord-052510c2e4af4be3abcee92997336ec4
Source dataset
uspto-grants-2013_05
Patent number
US08445515B2

Reaction notes

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