Triethylamine → (R)-(-)-1-CBZ-3-pyrrolidinol

HRID 2087086Notes

Reaction equation

HRID 2087086 reaction equation
[OH:1][C@@H:2]1[CH2:6][CH2:5][NH:4][CH2:3]1.C(N(CC)CC)C.Cl[C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16]>C(Cl)Cl>[OH:1][C@@H:2]1[CH2:6][CH2:5][N:4]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH2:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 2759337(R)-3-Pyrrolidinol

Product 1

HCID 11183628(R)-(-)-1-CBZ-3-pyrrolidinolYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

3-Hydroxy-(R)-pyrrolidine (8.71 g, 0.1 mol) was dissolved in CH2Cl2 (260 mL) and cooled to 0° C. Triethylamine (33.5 mL, 0.24 mol) and benzyl chloroformate (14.9 mL, 0.11 mol) were added, and the resulting solution was stirred for 2 h at 0° C. The solution was gradually warmed to room temperature and allowed to stir overnight. The solution was washed with 1 M HCl, saturated NaHCO3, and brine. The organic solution was dried over MgSO4 and concentrated. The crude product was purified by column chromatography eluting with ethyl acetate to afford 13.7 g (62% yield, 2 steps) of the desired product as a purple oil.

Workup

  1. temperatureThe solution was gradually warmed to room temperature
  2. stirringto stir overnight
  3. washThe solution was washed with 1 M HCl, saturated NaHCO3, and brine
  4. dry with materialThe organic solution was dried over MgSO4
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography
  7. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-e41e3b8ae9644341a26476706704a49b
Source dataset
uspto-grants-2004_04
Patent number
US06727368B1

Reaction notes

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