Tetrahydrofuran → HCID 58692303, compound

HRID 2054456Notes

Reaction equation

HRID 2054456 reaction equation
[Cu]C#N.[C:4]([C:6](=[C:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])#[N:5].O1[CH2:29][CH2:28][CH2:27][CH2:26]1>>[C:4]([CH:6]([C:12]1([C:26]2[CH:4]=[CH:6][C:12]([CH3:13])=[C:28]([CH3:29])[CH:27]=2)[CH2:13][CH2:14][N:15]([C:18]([O:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[O:19])[CH2:16][CH2:17]1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])#[N:5]

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran3×HCID 11551073TERT-BUTYL 4-(1-CYANO-2-ETHOXY-2-OXOETHYLIDENE)PIPERIDINE-1-CARBOXYLATEHCID 178418546HCID 178418546, compound

Product 1

HCID 58692303HCID 58692303, compound

Conditions

Temperature
-50 °C

Procedure

3,4-Dimethylmagnesium bromide (250 mL of a 0.5 M solution in tetrahydrofuran, 125 mmol, Rieke Metals, Inc., 3045) was added to a suspension of copper (I) cyanide (5.48 g, 61.2 mmol) in anhydrous tetrahydrofuran (400 mL) under nitrogen at approximately −50° C. After stirring at approximately −50° C. for 10 minutes, the reaction mixture was allowed to warm to ambient temperature over 1 h then recooled to approximately −50° C. A solution of tert-butyl 4-(1-cyano-2-ethoxy-2-oxoethylidene)piperidine-1-carboxylate 8-2 (15.0 g, 51.0 mmol) in tetrahydrofuran (50 mL) was added. After stirring at −50° C. for 3 h, the reaction mixture was warmed to 0° C. and quenched with saturated aqueous ammonium chloride. The mixture was extracted with ethyl acetate and the organic layer was washed with brine, dried (magnesium sulfate) and concentrated in vacuo to give compound 8-3 as light yellow oil.

Workup

  1. temperatureto warm to ambient temperature over 1 h
  2. customthen recooled to approximately −50° C
  3. stirringAfter stirring at −50° C. for 3 h
  4. temperaturethe reaction mixture was warmed to 0° C.
  5. customquenched with saturated aqueous ammonium chloride
  6. extractionThe mixture was extracted with ethyl acetate
  7. washthe organic layer was washed with brine
  8. dry with materialdried (magnesium sulfate)
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e2900e25c90445678fcbc24f4016a499
Source dataset
uspto-grants-2008_02
Patent number
US07329673B2

Reaction notes

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