HCID 54064258, compound → HCID 20672417, compound

HRID 1386791Notes

Reaction equation

HRID 1386791 reaction equation
CN(OC)[C:3](=[O:10])[C@@H:4]([CH:6]1[CH2:9][CH2:8][CH2:7]1)[CH3:5].[C:13]1([Li])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[CH:6]1([C@@H:4]([CH3:5])[C:3]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:9][CH2:8][CH2:7]1

Participants

3

Reactant 2

HCID 54064258HCID 54064258, compoundHCID 178506676HCID 178506676, compound

Product 1

HCID 20672417HCID 20672417, compoundYield 71.1%

Procedure

A dry flask was charged with N-Methyl-N-methoxy-(R)-2-cyclobutylpropionamide (2.62 grams, 15.4 mmol, from Step D). The vessel was purged with nitrogen and 40 mL THF was added. The mixture was cooled to −10 C and a solution of phenyllithium (30 mL, 1.8 M, 53.9 mmol) was added. The solution was stirred for 1 h at −10 C then the reaction was quenched with sat'd ammonium chloride. The mixture was extracted with ethyl acetate and the organic portion was dried over sodium sulfate and concentrated. Flash chromatography (99/1 hexane/ethyl acetate) afforded 2.06 grams (70%) of the title compound. 1H NMR 400 MHz, CDCl3). δ 1.13 (d, 3H), 1.59-1.7 (m, 1H), 1.73-2.0 (m, 5H), 2.05-2.15 (m, 1H), 2.6-2.7 (m, 1H), 3.43-3.53 (m, 1H), 7.44-7.5 (t, 2H), 7.55-7.6 (m, 1H), 7.97-8.0 (d, 2H).

Workup

  1. customThe vessel was purged with nitrogen and 40 mL THF
  2. additionwas added
  3. temperatureThe mixture was cooled to −10 C
  4. customthe reaction was quenched with sat'd ammonium chloride
  5. extractionThe mixture was extracted with ethyl acetate
  6. dry with materialthe organic portion was dried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4f16b7987f1c482795079e1f04c6f3e6
Source dataset
uspto-grants-2001_07
Patent number
US06265434B1

Reaction notes

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