Methanol → 5-Hydroxymethyl-1-(4-nitrophenyl)pyrrolidin-3-ol

HRID 719742Notes

Reaction equation

HRID 719742 reaction equation
[OH:1][CH:2]1[CH2:6][N:5]([C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=2)[CH:4]([C:16](O)=[O:17])[CH2:3]1.CO>C1COCC1>[OH:17][CH2:16][CH:4]1[N:5]([C:7]2[CH:8]=[CH:9][C:10]([N+:13]([O-:15])=[O:14])=[CH:11][CH:12]=2)[CH2:6][CH:2]([OH:1])[CH2:3]1

Participants

4

Reactant 2

HCID 887MethanolHCID 219018724-Hydroxy-1-(4-nitrophenyl)pyrrolidine-2-carboxylic acid

Product 1

HCID 219018155-Hydroxymethyl-1-(4-nitrophenyl)pyrrolidin-3-olYield 113%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5 g (19.8 mmol) of 4-hydroxy-1-(4-nitrophenyl)pyrrolidine-2-carboxylic acid were stirred in 50 ml of THF at 3° C. 60 ml (59 mmol) of borane-THF complex were added dropwise. The mixture was stirred at room temperature for 5 hours. Methanol was added slowly. The reaction mixture was evaporated to dryness. The product was precipitated from saturated sodium chloride solution, filtered off and dried under vacuum. 5.33 g of a yellow powder were obtained.

Workup

  1. addition60 ml (59 mmol) of borane-THF complex were added dropwise
  2. customThe reaction mixture was evaporated to dryness
  3. customThe product was precipitated from saturated sodium chloride solution
  4. filtrationfiltered off
  5. customdried under vacuum

Sources & evidence

ORD record
ord-9b5520f1cc3d43afb3e70a206620a3a3
Source dataset
uspto-grants-2006_11
Patent number
US07132543B2

Reaction notes

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