Tetrahydrofuran → Methyl 2-allyloctanoate

HRID 1180697Notes

Reaction equation

HRID 1180697 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>>[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

4

Reactant 3

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

Product 1

HCID 23117480Methyl 2-allyloctanoate

Procedure

A solution of 25.12 g (67.5 mmol) of N-isopropyloxycarbonyl-N-(2-allyloctanoyl)-1-(R)-phenylethylamine ((1R,2S):(1R,2R)=77:23) in 338 ml of THF was cooled to −10° C., 26.1 g (135 mmol) of NaOMe (28% solution in methanol) was added dropwise and, after completion of the addition, the mixture was further stirred for 45 minutes. The reaction was terminated by addition of 120 ml of 1 N hydrochloric acid, and the product was extracted with hexane (100 ml×2). The extract was dried over anhydrous sodium sulfate, and the solvent was distilled off to give 25.90 g of a crude product. This was purified on a silica gel column to give 12.32 g (92%, 54% ee) of the title compound.

Workup

  1. additionafter completion of the addition
  2. customThe reaction was terminated by addition of 120 ml of 1 N hydrochloric acid
  3. extractionthe product was extracted with hexane (100 ml×2)
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off
  6. customto give 25.90 g of a crude product
  7. customThis was purified on a silica gel column

Sources & evidence

ORD record
ord-0744b398317c4f2391884bd7a8f67fd8
Source dataset
uspto-grants-2007_10
Patent number
US07282605B2

Reaction notes

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