Sulfuric Acid → N-[4-(Hydroxymethyl)-2-cyclopenten-1-yl]butanamide

HRID 750425Notes

Reaction equation

HRID 750425 reaction equation
[C:1]([N:6]1[C:11](=[O:12])[CH:10]2[CH2:13][CH:7]1[CH:8]=[CH:9]2)(=[O:5])[CH2:2][CH2:3][CH3:4].[BH4-].[Na+].S(=O)(=O)(O)O.C(OCC)(=O)C>C(O)C>[C:1]([NH:6][CH:7]1[CH2:13][CH:10]([CH2:11][OH:12])[CH:9]=[CH:8]1)(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 226732852-Butanoyl-2-azabicyclo[2.2.1]hept-5-EN-3-one

Product 1

HCID 22673280N-[4-(Hydroxymethyl)-2-cyclopenten-1-yl]butanamideYield 80.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
-10 °C

Procedure

73.87 g of (±)-2-butyryl-2-azabicyclo[2.2.1]hept-5-en-3-one were dissolved in ethanol (400 ml) under nitrogen and cooled to −10° C. 15.68 g of sodium borohydride were added in portions over the course of 45 minutes. The reaction was stirred at 0° C. for 3 hours and then the pH was adjusted to 1.5 with conc. sulphuric acid. Ethyl acetate (200 ml) was added to this mixture, and the solids were filtered off. It was then completely evaporated. The residue was taken up in water, washed with methylene chloride, evaporated and dried under high vacuum. 60.55 g of product were obtained. The yield was 80% based on (±)-2-butyryl-2-azabicyclo[2.2.1]hept-5-en-3-one employed.

Workup

  1. filtrationthe solids were filtered off
  2. customIt was then completely evaporated
  3. washwashed with methylene chloride
  4. customevaporated
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-430e7364fcd64cd3a96ecda7f8df86a5
Source dataset
uspto-grants-2008_07
Patent number
US07405065B2

Reaction notes

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