Tetrahydrofuran → Methyl 2-allyloctanoate

HRID 1180699Notes

Reaction equation

HRID 1180699 reaction equation
C(OC(N([C@@H](C1C=CC=CC=1)C)C(=O)[CH:9]([CH2:16][CH:17]=[CH2:18])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])=O)(C)C.[CH3:28][O-:29].[Na+].C1C[O:34][CH2:33]C1>CO>[CH2:13]([CH:12]([CH2:11][CH2:10][CH2:9][CH2:16][CH2:17][CH3:18])[C:28]([O:34][CH3:33])=[O:29])[CH:14]=[CH2:15]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 10942334Sodium MethoxideHCID 69502054N-Isopropyloxycarbonyl-N-(2-allyloctanoyl)-(R)-1-phenylethylamine

Product 1

HCID 23117480Methyl 2-allyloctanoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 0.374 g (1.0 mmol) of N-isopropyloxycarbonyl-N-(2-allyloctanoyl)-1-(R)-phenylethylamine ((1R,2S):(1R,2R)=77.6:22.4) in 5 ml of THF was cooled to 0° C. A solution of 11 mg (0.2 mmol) of NaOMe in methanol (0.04 g) was added, and the mixture was stirred for 7 hours. The reaction was terminated by addition of 1 ml of 1 N hydrochloric acid, and the product was extracted with ethyl acetate (30 ml×2). The extract was dried over anhydrous sodium sulfate, and the solvent was distilled off. The residue was quantitated by GC. Thus was obtained 0.163 g (82%, 55.0% ee) of the title compound.

Workup

  1. customThe reaction was terminated by addition of 1 ml of 1 N hydrochloric acid
  2. extractionthe product was extracted with ethyl acetate (30 ml×2)
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-56bcdcdd8cd44e3fbc51570e68e76f86
Source dataset
uspto-grants-2007_10
Patent number
US07282605B2

Reaction notes

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