Ethyl Acetate → (S)-3-[6-(2-methoxy-phenyl)-pyrimidin-4-ylcarbamoyl]-piperidine-1-carboxylic acid benzyl ester

HRID 1020057Notes

Reaction equation

HRID 1020057 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:14]=[CH:13][N:12]=[C:11]([NH2:15])[CH:10]=1.[CH2:16]([O:23][C:24]([N:26]1[CH2:31][CH2:30][CH2:29][C@H:28]([C:32](Cl)=[O:33])[CH2:27]1)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(OCC)(=O)C>ClCCl.CN(C)C1C=CN=CC=1.CCCCCC>[CH2:16]([O:23][C:24]([N:26]1[CH2:31][CH2:30][CH2:29][C@H:28]([C:32](=[O:33])[NH:15][C:11]2[CH:10]=[C:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[O:2][CH3:1])[N:14]=[CH:13][N:12]=2)[CH2:27]1)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 3

HCID 8857Ethyl AcetateHCID 7015654(S)-3-chlorocarbonyl-piperidine-1-carboxylic acid benzyl esterHCID 497584396-(2-Methoxyphenyl)pyrimidin-4-amine

Product 1

HCID 59509033(S)-3-[6-(2-methoxy-phenyl)-pyrimidin-4-ylcarbamoyl]-piperidine-1-carboxylic acid benzyl esterYield 54%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

To a solution of 6-(2-methoxy-phenyl)-pyrimidin-4-ylamine (XXIV) (7.80 g, 39.1 mmol) in 90 ml of dichloromethane was added 4-dimethylaminopyridine (5.70 g, 47.0 mmol) followed by dropwise addition of N—(S)-3-chlorocarbonyl-piperidine-1-carboxylic acid benzyl ester (XXXIII) (11.0 g, 39.1 mmol) at room temperature. The reaction mixture was stirred for 2 hours and washed with water. The organic layer was separated, dried over sodium sulfate and concentrated. The obtained crude residue was passed through a pad of silica gel eluting with 25% ethyl acetate in hexane to provide (S)-3-[6-(2-methoxy-phenyl)-pyrimidin-4-ylcarbamoyl]-piperidine-1-carboxylic acid benzyl ester (XXXIV) (9.4 g, 54%).

Workup

  1. washwashed with water
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe obtained crude residue

Sources & evidence

ORD record
ord-95584b4ea3e940b88edfab8158967d5a
Source dataset
uspto-grants-2014_05
Patent number
US08716296B2

Reaction notes

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