Water → Phenylmethyl (3R)-3-[[(1,1-dimethylethoxy)carbonyl]amino]-1-pyrrolidinecarboxylate

HRID 1663595Notes

Reaction equation

HRID 1663595 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:13][CH2:12][NH:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH2:21]([O:28][C:29](Cl)=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.O>C(Cl)Cl>[CH2:21]([O:28][C:29]([N:11]1[CH2:12][CH2:13][C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:10]1)=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 1514397(3R)-(+)-3-(tert-Butoxycarbonylamino)pyrrolidine

Product 1

HCID 14555480Phenylmethyl (3R)-3-[[(1,1-dimethylethoxy)carbonyl]amino]-1-pyrrolidinecarboxylateYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (3R)-3-(tert-butyloxycarbonylamino)pyrrolidine (10.0 g) and triethylamine (5.43 g) in methylene chloride (100 mL) was added dropwise a solution of benzyloxycarbonyl chloride (7.7 mL) in methylene chloride (20 mL) over a period of 15 minutes under nitrogen gas atmosphere and ice-cooling and the mixture was stirred at room temperature for 1 hour. To the reaction mixture was added water (70 mL) and the mixture was extracted with chloroform. The extract was washed successively with water (70 mL), 5% citric acid solution (70 mL) and a saturated brine (70 mL) and the organic layer was dried over anhydrous magnesium sulfate. After concentration in vacuo, the resultant product was triturated in diisopropylether to give (3R)-1-benzyloxycarbonyl-3-(tert-butoxycarbonylamino)pyrrolidine (11.8 g, yield: 70%) as crystals.

Workup

  1. temperatureice-cooling
  2. extractionthe mixture was extracted with chloroform
  3. washThe extract was washed successively with water (70 mL), 5% citric acid solution (70 mL)
  4. dry with materiala saturated brine (70 mL) and the organic layer was dried over anhydrous magnesium sulfate
  5. concentrationAfter concentration in vacuo
  6. customthe resultant product was triturated in diisopropylether

Sources & evidence

ORD record
ord-cf0fd6c84ea5452ebaf7a7d388b15d93
Source dataset
uspto-grants-2011_10
Patent number
US08034949B2

Reaction notes

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