Hydrochloric Acid → (S)-(-)-1-Benzyl-3-pyrrolidinol

HRID 1081434Notes

Reaction equation

HRID 1081434 reaction equation
S(=O)(=O)(O)O.[CH2:6]([N:13]1[C:17](=O)[CH2:16][C@H:15]([OH:19])[C:14]1=O)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.B.[Na].Cl>COCCOC.C1(C)C=CC=CC=1.O.CO>[CH2:6]([N:13]1[CH2:17][CH2:16][C@H:15]([OH:19])[CH2:14]1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 10954694(S)-1-benzyl-3-hydroxypyrrolidine-2,5-dioneHCID 178418435HCID 178418435, compound

Product 1

HCID 2733875(S)-(-)-1-Benzyl-3-pyrrolidinolYield 97.9%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 1140TolueneSolventHCID 80711,2-DimethoxyethaneSolvent2×

Procedure

A solution of 13.4 ml (0.25 mole) sulfuric acid in 40 ml DME was added dropwise to a suspension of 25.6 g (0.125 mole) (S)-1-benzyl-3-hydroxy-2,5-pyrrolidine dione (IIa) and 19 g (0.5 mole) sodium boron hydride in 150 ml DME within 1.5 h at 35° C. The mixture was subsequently agitated 2 h at 70° C. After cooling off, 40 ml MeOH were added and the batch was evaporated to dryness. The residue was taken up in 120 ml water and agitated overnight at room temperature with 30 ml conc. hydrochloric acid and 150 ml toluene. After alkalization with 45 ml 50% sodium hydroxide solution the toluene phase was separated off at 70° C. and the aqueous phase subsequently extracted [re-extracted] with 100 ml toluene. The toluene phases were evaporated to dryness after drying over sodium sulfate, during which 22.7 g oil were obtained. It was taken up in 150 ml toluene, 100 ml water and 15 ml conc. hydrochloric acid and agitated overnight at room temperature. After repetition of the described workup 21.7 g (97.9%) (S)-1-benzyl-3-hydroxypyrrolidine (IIIa) were obtained as oil.

Workup

  1. temperatureAfter cooling off
  2. customthe batch was evaporated to dryness
  3. customAfter alkalization with 45 ml 50% sodium hydroxide solution the toluene phase was separated off at 70° C.
  4. extractionthe aqueous phase subsequently extracted
  5. extraction[re-extracted] with 100 ml toluene
  6. customThe toluene phases were evaporated to dryness
  7. dry with materialafter drying over sodium sulfate, during which 22.7 g oil
  8. customwere obtained

Sources & evidence

ORD record
ord-0a07c365a60b489e8ff7d610dc332ba8
Source dataset
uspto-grants-1996_12
Patent number
US05585500

Reaction notes

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