Trifluoroacetic acid → (3S,5S)-5-(Hydroxymethyl)-3-(propan-2-yl)pyrrolidin-2-one

HRID 1099317Notes

Reaction equation

HRID 1099317 reaction equation
[CH:1]([C@H:4]1[C:17](=[O:18])[N:7]2[C@@H](C3C=CC=CC=3)[O:9][CH2:10][C@@H:6]2[CH2:5]1)([CH3:3])[CH3:2].FC(F)(F)C(O)=O>ClCCl>[OH:9][CH2:10][C@H:6]1[NH:7][C:17](=[O:18])[C@H:4]([CH:1]([CH3:3])[CH3:2])[CH2:5]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 11536081HCID 11536081, compound

Product 1

HCID 40479237(3S,5S)-5-(Hydroxymethyl)-3-(propan-2-yl)pyrrolidin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 16.5 g of (3R,6S,7aS)-6-isopropyl-3-phenyltetrahydro-pyrrolo[1,2-c]oxazol-5-one in 175 mL of dichloromethane is treated with 15.35 g of trifluoroacetic acid at room temperature. The resulting solution is stirred for 24 hours at room temperature and a further 14 g of trifluoroacetic acid added. Stirring is continued for a further 24 hours and the solvent removed in vacuum. The residue is treated with 50 mL of water and 100 mL of dichloromethane and the pH of the two-phase mixture adjusted to 12 with concentrated sodium hydroxide solution. Solid sodium chloride is added and the mixture stirred. The organic layer is removed under reduced pressure to give (3S,5S)-5-hydroxymethyl-3-isopropyl-pyrrolidin-2-one as a semi-solid. mp. 55.9° C., [α]D=+47.9° (1% in MeOH)

Workup

  1. stirringStirring
  2. waitis continued for a further 24 hours
  3. customthe solvent removed in vacuum
  4. additionThe residue is treated with 50 mL of water and 100 mL of dichloromethane
  5. additionSolid sodium chloride is added
  6. stirringthe mixture stirred
  7. customThe organic layer is removed under reduced pressure

Sources & evidence

ORD record
ord-e7b9cdb86c2d48bd8b02cd8cd22eb50a
Source dataset
uspto-grants-2012_03
Patent number
US08143416B2

Reaction notes

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