Benzyl chloroformate → HCID 51041670, compound

HRID 17633Notes

Reaction equation

HRID 17633 reaction equation
[CH3:1][C@:2]1([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:6][CH2:5][NH:4][CH2:3]1.C(=O)([O-])O.[Na+].[CH2:20]([O:27][C:28](Cl)=[O:29])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(OCC)C>[C:10]([O:9][C:8]([NH:7][C@@:2]1([CH3:1])[CH2:6][CH2:5][N:4]([C:28]([O:27][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:29])[CH2:3]1)=[O:14])([CH3:13])([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 51041669(S)-tert-Butyl (3-methylpyrrolidin-3-yl)carbamate

Product 1

HCID 51041670HCID 51041670, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

tert-Butyl [(3S)-3-methylpyrrolidin-3-yl]carbamate (I-345) (240 mg, 1.20 mmol) was dissolved in diethyl ether (12 ml), then an aqueous saturated sodium hydrogencarbonate solution (12 ml) was added, and at room temperature, benzyloxycarbonyl chloride (222 μl, 1.56 mmol) was added, followed by stirring at room temperature for 16 hours. The reaction liquid was extracted with ethyl acetate, and the obtained organic layer was washed with saturated brine. After drying over anhydrous sodium sulfate, the insoluble matter was separated by filtration, and the residue obtained by concentration was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=2:1, v/v) to obtain the entitled compound (400 mg, 100%) as a colorless oily substance.

Workup

  1. customThe reaction liquid
  2. extractionwas extracted with ethyl acetate
  3. washthe obtained organic layer was washed with saturated brine
  4. dry with materialAfter drying over anhydrous sodium sulfate
  5. customthe insoluble matter was separated by filtration
  6. customthe residue obtained by concentration
  7. customwas purified by silica gel column chromatography (eluent, n-hexane

Sources & evidence

ORD record
ord-d1b22753ac054d1f9e6c34ae429269ae
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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