Benzyl chloroformate → HCID 66799345, compound

HRID 1193377Notes

Reaction equation

HRID 1193377 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7][O:8][C:9](Cl)=[O:10])=[CH:3][CH:2]=1.[CH3:12][NH:13][CH:14]1[CH2:19][CH2:18][NH:17][C:16](=[O:20])[CH2:15]1.C([O-])([O-])=O.[K+].[K+]>C1COCC1.C(Cl)Cl>[CH3:12][N:13]([CH:14]1[CH2:19][CH2:18][NH:17][C:16](=[O:20])[CH2:15]1)[C:9](=[O:10])[O:8][CH2:7][C:4]1[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1

Participants

6

Reactant 3

HCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 66798914HCID 66798914, compound

Product 1

HCID 66799345HCID 66799345, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Cbz-Cl (7.2 ml, 21.259 mol, 1.5 eq., 50% solution in toluene) was added at 0° C. to a mixture of 4-(methylamino)piperidin-2-one (1.814 g, 14.173 mmol, 1.0 eq.) and K2CO3 (3.91 g, 28.346 mmol, 2.0 eq.) in THF (50 ml) and the mixture was stirred for 14 hours at RT. After monitoring by TLC, the reaction mixture was diluted with DCM (300 ml), washed with water and saturated NaCl solution (in each case 150 ml), dried over sodium sulfate, concentrated under reduced pressure and purified by column chromatography (Alox, 1% MeOH in DCM). Yield: 27% (1.0 g, 3.82 mmol)

Workup

  1. washwashed with water and saturated NaCl solution (in each case 150 ml),
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. custompurified by column chromatography (Alox, 1% MeOH in DCM)

Sources & evidence

ORD record
ord-9fa7d4f23b3241e4a3a3b2a74eaf1252
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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