Sodium Chloride → (R)-(-)-1-CBZ-3-pyrrolidinol

HRID 2073173Notes

Reaction equation

HRID 2073173 reaction equation
[CH2:1]1[C@@H:5]([OH:6])[CH2:4][NH:3][CH2:2]1.Cl.[OH-].[Na+].[C:10](Cl)([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11].[Cl-].[Na+]>O>[OH:6][C@@H:5]1[CH2:1][CH2:2][N:3]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH2:4]1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 10387Benzyl chloroformateHCID 14798Sodium Hydroxide2×HCID 2759336(3R)-pyrrolidin-3-ol hydrochloride

Product 1

HCID 11183628(R)-(-)-1-CBZ-3-pyrrolidinolYield 95.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 10.2 g (82.6 mmol) of R-3-hydroxypyrrolidine hydrochloride (Chem. Letts., 1966, pp 893-6) in 50 m of water was cooled to 0° and treated with 22.5 ml (90 mmol) of 4.0 N sodium hydroxide. The neutral solution was treated dropwise with 15.6 g (87 mmol) of carbobenzyloxy chloride maintaining the pH at 11.0±0.5 by the dropwise addition of 87 ml of 1.0 N sodium hydroxide and the temperature below 5° with a salt-ice bath. When the addition was complete, the mixture was stirred at 5° for two hours and stored at 5° for 18 hours. The reaction mixture was saturated with sodium chloride and extracted with ethyl acetate (2 ×500 ml). The combined organic layers were washed with 1.0 N sodium hydroxide (4×50 ml), water, dried (MgSO4) and evaporated in vacuo to give 17.5 g of the title compound.

Workup

  1. customthe temperature below 5°
  2. additionWhen the addition
  3. waitstored at 5° for 18 hours
  4. extractionextracted with ethyl acetate (2 ×500 ml)
  5. washThe combined organic layers were washed with 1.0 N sodium hydroxide (4×50 ml), water
  6. dry with materialdried (MgSO4)
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-dd149774a3224a2782226b2462349db5
Source dataset
uspto-grants-1990_04
Patent number
US04916141

Reaction notes

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