4-Methylmorpholine → (2S)-1-(phenylmethyl)-2-(1-pyrrolidinylcarbonyl)piperidine

HRID 1366695Notes

Reaction equation

HRID 1366695 reaction equation
Cl.[C:2]1([CH2:8][N:9]2[CH2:16][CH2:15][CH2:14][C@H:10]2[C:11]([OH:13])=O)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:17]1[CH:18]=CC2N(O)N=[N:23][C:21]=2[CH:22]=1.[CH3:27]N1CCOCC1.N1CCCCC1.CCN=C=NCCCN(C)C>C(Cl)Cl>[C:2]1([CH2:8][N:9]2[CH2:16][CH2:15][CH2:14][CH2:27][C@H:10]2[C:11]([N:23]2[CH2:18][CH2:17][CH2:22][CH2:21]2)=[O:13])[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 8082PiperidineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 573677341-Benzyl-L-proline hydrochloride

Product 1

HCID 66936271(2S)-1-(phenylmethyl)-2-(1-pyrrolidinylcarbonyl)piperidineYield 40.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(Phenylmethyl)-L-proline hydrochloride (2.0 g, 8.247 mmol) and HOBt (1.34 g, 9.928 mmol) were dissolved in CH2Cl2 (50 mL), and 4-methylmorpholine (2.72 mL, 24.822 mmol), piperidine (0.981 mL, 9.929 mmol), and EDCI (1.906 g, 9.928 mmol) were added to this solution. After stirring overnight, the solution was washed with water (50 mL), and the aqueous layer was extracted with CH2Cl2 (3×50 mL). The combined organic layers were dried over anhydrous MgSO4 and concentrated in vacuo to provide (2S)-1-(phenylmethyl)-2-(1-pyrrolidinylcarbonyl)piperidine (0.901 g, 40%). LCMS: (M+H)+: 273.1.

Workup

  1. washthe solution was washed with water (50 mL)
  2. extractionthe aqueous layer was extracted with CH2Cl2 (3×50 mL)
  3. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6178d18268e24c79b11e6c0f04b26a34
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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