Methanol → HCID 15046660, compound

HRID 2107969Notes

Reaction equation

HRID 2107969 reaction equation
[CH2:1]([NH2:4])[C:2]#[CH:3].[C:5](=[O:8])([O-])[O-].[Na+].[Na+].CC[O:13][CH2:14][CH3:15].[CH3:16]O>>[OH:13][C@H:14]1[CH2:15][CH2:16][N:4]([CH2:1][C:2]#[CH:3])[C:5]1=[O:8]

Participants

5

Reactant 4

HCID 887Methanol2×HCID 3283Diethyl EtherHCID 10340Sodium CarbonateHCID 239041Propargylamine

Product 1

HCID 15046660HCID 15046660, compound

Procedure

A solution of the above solid in methanol was added dropwise to an equimolar amount of propargylamine and sodium carbonate in 500 ml of methanol. The mixture was stirred at room temperature for 1.5 hours, then heated at reflux overnight. Ether was added, the mixture was filtered and the filtrate concentrated to an oil. The oil was concentrated from toluene and then chromatographed (silica gel), giving 25 g of (S)-3-hydroxy-1-(2-propynyl)-2-pyrrolidinone [α]D260 =-99° (dichloromethane); mp 89°-90° C.

Workup

  1. temperatureheated
  2. temperatureat reflux overnight
  3. filtrationthe mixture was filtered
  4. concentrationthe filtrate concentrated to an oil
  5. concentrationThe oil was concentrated from toluene
  6. customchromatographed (silica gel)

Sources & evidence

ORD record
ord-ace520fbff1f4273a22e746fef6f57bf
Source dataset
uspto-grants-1990_06
Patent number
US04937235

Reaction notes

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