2-Pyrrolidone → HCID 67884023, compound

HRID 1613597Notes

Reaction equation

HRID 1613597 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].Br[C@@H:12]1[C:18]2[CH:19]=[C:20]([Cl:23])[CH:21]=[CH:22][C:17]=2[O:16][CH2:15][CH2:14][C@H:13]1[OH:24].[NH:25]1[CH2:29][CH2:28][CH2:27][C:26]1=[O:30]>>[Cl:23][C:20]1[CH:21]=[CH:22][C:17]2[O:16][CH2:15][CH2:14][C@@H:13]([OH:24])[C@H:12]([N:25]3[CH2:29][CH2:28][CH2:27][C:26]3=[O:30])[C:18]=2[CH:19]=1

Participants

4

Reactant 3

HCID 120252-PyrrolidoneHCID 2733832Lithium Hexamethyldisilazide2×HCID 67883885HCID 67883885, compound

Product 1

HCID 67884023HCID 67884023, compound

Conditions

Temperature
110 °C

Procedure

5 ml (5 mmol) of lithium bis-(trimethylsilyl)-amide (1M solution in THF) are added dropwise with stirring to 1.40 g (5 mmol) of trans-5-bromo-7-chloro-4-hydroxy-2,3,4,5-tetrahydro-1-benzoxepin at 0° C. under argon. After stirring for 2 hours, 0.43 g (5 mmol) of 2-pyrrolidinone and subsequently a further 5 ml of lithium bis-(trimethylsilyl)-amide are added, and the mixture is heated at 110° C. for several hours (TLC check). The mixture is poured onto ice-water and extracted several times with ethyl acetate. The combined ethyl acetate extracts are washed with water and saturated sodium chloride solution, dried over sodium sulfate, filtered and evaporated in vacuo. The residue is triturated with hot methanol/ethyl acetate and filtered off with suction. Crystals of melting point 186°-188° C. are obtained.

Workup

  1. additionThe mixture is poured onto ice-water
  2. extractionextracted several times with ethyl acetate
  3. washThe combined ethyl acetate extracts are washed with water and saturated sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue is triturated with hot methanol/ethyl acetate
  8. filtrationfiltered off with suction
  9. customCrystals of melting point 186°-188° C. are obtained

Sources & evidence

ORD record
ord-94afed16be444096b9e2ffea6bd73c9a
Source dataset
uspto-grants-1993_03
Patent number
US05194442

Reaction notes

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