Benzyl chloroformate → HCID 60204906, compound

HRID 1245034Notes

Reaction equation

HRID 1245034 reaction equation
C(=O)([O-])O.[Na+].Cl[C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8].[CH3:17][O:18][C:19](=[O:26])[C@@H:20]1[CH2:24][CH:23]([CH3:25])[CH2:22][NH:21]1>C1(C)C=CC=CC=1>[CH3:17][O:18][C:19](=[O:26])[C@@H:20]1[CH2:24][CH:23]([CH3:25])[CH2:22][N:21]1[C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8]

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 45089984HCID 45089984, compound

Product 1

HCID 60204906HCID 60204906, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

20 ml of an aqueous solution containing 1.89 g (22.5 mmol) of sodium hydrogencarbonate and 1.54 ml (10.8 mmol) of benzyl chloroformate were added to a solution of 0.93 g (6.5 mmol) of (2S)-4-methylproline methyl ester [obtained as described in Preparative Example 8(ii)′ above] in 20 ml of toluene, and the resulting mixture was stirred at room temperature over night. At the end of this time, the reaction mixture was extracted with ethyl acetate. The organic extract was washed with water and concentrated under reduced pressure to afford 1.78 g (yield: 99%) of (2S)-1-benzyloxycarbonyl-4-methylproline methyl ester as a pale yellow oil. Subsequently, all of the compound thus obtained was reduced using lithium borohydride, in a similar manner to that described in Preparative Example 5(i)′ above, to afford 1.07 g (yield: 66%) of the title compound as a pale yellow oil.

Workup

  1. customobtained
  2. extractionAt the end of this time, the reaction mixture was extracted with ethyl acetate
  3. extractionThe organic extract
  4. washwas washed with water
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a546b5f1ac6d4bee8327040ac9a6e78f
Source dataset
uspto-grants-2006_10
Patent number
US07122666B2

Reaction notes

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