Benzyl chloroformate → HCID 14987157, compound

HRID 2051519Notes

Reaction equation

HRID 2051519 reaction equation
[CH2:1]([O:8][C:9](Cl)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].[CH3:17][C@H:18]1[C@@H:23]([NH:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[F:31])[CH2:22][CH2:21][NH:20][CH2:19]1>O.CCOCC>[CH2:1]([O:8][C:9]([N:20]1[CH2:21][CH2:22][C@H:23]([NH:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[F:31])[C@H:18]([CH3:17])[CH2:19]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 14987156HCID 14987156, compound

Product 1

HCID 14987157HCID 14987157, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

To a rapidly stirred mixture of benzylchloroformate (0.39 ml, 2.76 mmol) and sodium bicarbonate (284 mg, 3.6 mmol) in water (4 ml) and ether (4 ml) is added cis-3-methyl-4-(2-fluoro-phenylamino)-piperidine (500 mg, 2.4 mmol) as a solution in ether (2 ml). The mixture is stirred for one hour at ambient temperature, the layers are separated, and the organics washed with 2N NaOH (2×) and brine (1×). The organics are dried over sodium sulfate and concentrated to give cis-1-benzyloxycarbonyl-3-methyl-4-(2-fluorophenylamino)-piperidine as an oil: 740 mg; 90%.

Workup

  1. customthe layers are separated
  2. washthe organics washed with 2N NaOH (2×) and brine (1×)
  3. dry with materialThe organics are dried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-893d86e01613419781b30c9c703e34b7
Source dataset
uspto-grants-1991_05
Patent number
US05019583

Reaction notes

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