Dimethylamine → phenylmethyl (2S)-2-[(dimethylamino)carbonyl]-1-piperidinecarboxylate

HRID 1366698Notes

Reaction equation

HRID 1366698 reaction equation
[C:1]1([CH2:7][O:8][C:9]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]2[C:17]([OH:19])=O)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C=CC2N(O)N=NC=2C=1.[CH3:30][N:31]1CCOC[CH2:32]1.CNC.C1COCC1.CCN=C=NCCCN(C)C>C(Cl)Cl>[CH3:30][N:31]([CH3:32])[C:17]([C@@H:12]1[CH2:13][CH2:14][CH2:15][CH2:16][N:11]1[C:9]([O:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:10])=[O:19]

Participants

8

Reactant 6

HCID 674DimethylamineHCID 79724-MethylmorpholineHCID 8028TetrahydrofuranHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 688345(S)-1-N-Cbz-Pipecolinic acid

Product 1

HCID 66936339phenylmethyl (2S)-2-[(dimethylamino)carbonyl]-1-piperidinecarboxylateYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2S)-1-{[(Phenylmethyl)oxy]carbonyl}-2-piperidinecarboxylic acid (2.0 g, 7.595 mmol) and HOBt (1.231 g, 9.114 mmol) were dissolved in CH2Cl2 (40 mL), and 4-methylmorpholine (2.5 mL, 22.78 mmol), 2.0 M solution of dimethyl amine in THF (4.55 mL, 9.114 mmol), and EDCI (1.750 g, 9.114 mmol) were added. This solution was stirred overnight, and was then washed with 1 N HCl (25 mL) and the aqueous layer was extracted with CH2Cl2 (3×25 mL). The combined organic layers were dried over anhydrous MgSO4 and concentrated in vacuo. This crude product was purified by flash chromatography (Combiflash, 0-100% ethyl acetate/hexanes) to provide phenylmethyl (2S)-2-[(dimethylamino)carbonyl]-1-piperidinecarboxylate (1.919 g, 87%). LCMS: (M+H)+: 291.1.

Workup

  1. washwas then washed with 1 N HCl (25 mL)
  2. extractionthe aqueous layer was extracted with CH2Cl2 (3×25 mL)
  3. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  4. concentrationconcentrated in vacuo
  5. customThis crude product was purified by flash chromatography (Combiflash, 0-100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-e923d4e571774ab9a6e5c9184b4c7716
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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