Acetic Acid → HCID 59376115, compound

HRID 2273867Notes

Reaction equation

HRID 2273867 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-5360c4971fa24c428f575321773696ca
Source dataset
uspto-grants-2015_09
Patent number
US09126939B2

Reaction notes

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