Benzyl chloroformate → benzyl 2-(hydroxymethyl)pyrrolidine-1-carboxylate

HRID 2300801Notes

Reaction equation

HRID 2300801 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[CH2:6][OH:7].C([O-])(O)=O.[Na+].[CH2:13]([O:20][C:21](Cl)=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(Cl)Cl>[CH2:13]([O:20][C:21]([N:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[CH2:6][OH:7])=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 90908ProlinolHCID 516892Sodium Bicarbonate

Product 1

HCID 4576020benzyl 2-(hydroxymethyl)pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Pyrrolidinemethanol (2 g, 20 mmol) was dissolved in CH2Cl2 (25 mL) followed by addition of saturated NaHCO3 (25 mL). To this vigorously stirred mixture was added benzylchloroformate via syringe slowly at 0° C. The reaction mixture was then stirred at room temperature for 4 h. The organic layer was separated and the aqueous layer was extracted with CH2Cl2 (3×80 mL). The combined organic layer was washed with brine, and dried (Na2SO4). Removal of the solvent provided 4.7 g of the title compound, which was used, directly for next step. 1H NMR (CDCl3): δ 7.50-7.30 (aromatic Hs, 5H); 5.17 (s, 2H); 4.04 (brs, 1H); 3.66 (m, 2H); 3.57 (m, 1H); 3.42 (m, 1H); 2.04 (m, 1H); 1.89 (m, 1H); 1.83 (m, 1H); 1.62 (m, 1H).

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with CH2Cl2 (3×80 mL)
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried (Na2SO4)
  5. customRemoval of the solvent

Sources & evidence

ORD record
ord-162adbc385364062ae49bee37a0ce984
Source dataset
uspto-grants-2002_12
Patent number
US06498165B1

Reaction notes

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