Benzyl chloroformate → HCID 58376763, compound

HRID 1942481Notes

Reaction equation

HRID 1942481 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[CH2:5][C@H:6]1[CH2:11][CH2:10][C@@H:9]([NH:12][CH:13]([CH3:15])[CH3:14])[CH2:8][N:7]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH3:2].C(N(C(C)C)CC)(C)C.[CH:33]1[CH:38]=[CH:37][C:36]([CH2:39][O:40][C:41](Cl)=[O:42])=[CH:35][CH:34]=1>ClCCl.C(Cl)(Cl)Cl>[CH2:39]([O:40][C:41]([N:12]([CH:13]([CH3:14])[CH3:15])[C@H:9]1[CH2:8][N:7]([C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[C@@H:6]([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:23])[CH2:11][CH2:10]1)=[O:42])[C:36]1[CH:37]=[CH:38][CH:33]=[CH:34][CH:35]=1

Participants

6

Reactant 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 58376487HCID 58376487, compound

Product 1

HCID 58376763HCID 58376763, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (2R,5R)-2-(2-ethoxy-2-oxoethyl)-5-(isopropylamino)piperidine-1-carboxylate (6.0 g) in dichloromethane (200 mL) was added diisopropylethylamine (19.1 mL), and thereto was further added dropwise under ice-cooling Z—Cl (13.0 mL) over a period of one hour. The mixture was stirred at room temperature for one hour, and then, the reaction solution was diluted with chloroform. The mixture was washed successively with an ice-cold aqueous potassium hydrogen sulfate solution and a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel chromatography to give the title compound (8.9 g) as a pale brown oil.

Workup

  1. additionwas further added dropwise under ice-
  2. washThe mixture was washed successively with an ice-cold aqueous potassium hydrogen sulfate solution
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-1de06f7fd9fb47e4bb3faecfbf084f02
Source dataset
uspto-grants-2013_03
Patent number
US08389511B2

Reaction notes

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