Hydrochloric Acid → HCID 57891190, compound

HRID 2047178Notes

Reaction equation

HRID 2047178 reaction equation
[CH3:1][C:2]#[N:3].[Li]CCCC.C[O:10][C:11](=O)[CH2:12][CH:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1.Cl>C1COCC1>[C:2]([CH2:1][C:11](=[O:10])[CH2:12][CH:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:24])([CH3:23])[CH3:25])=[O:20])[CH2:15][CH2:14]1)#[N:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 1514280tert-Butyl 4-(2-methoxy-2-oxoethyl)piperidine-1-carboxylateHCID 178418339Butyllithium

Product 1

HCID 57891190HCID 57891190, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-78 °C

Procedure

At −78° C., CH3CN in THF (1505 uL, 28.82 mmoL) was added dropwise to BuLi (2.5 M in hexane, 11.52 mL) in THF (40 mL). After stirring at −78° C. for 1 h, tert-butyl 4-(2-methoxy-2-oxoethyl)piperidine-1-carboxylate (3708 mg, 14.41 mmoL) in THF (10 mL) was added dropwise in 5 min. The mixture was stirred at −78° C. for 1 h and −45° C. for 1 h. At 0° C., 1N HCl was added carefully to adjust the pH to about 7. The mixture was then extracted with ethyl acetate (×2). The combined organic layers were washed with brine and dried with Na2SO4. Evaporation afforded tert-butyl 4-(3-cyano-2-oxopropyl)piperidine-1-carboxylate.

Workup

  1. stirringThe mixture was stirred at −78° C. for 1 h and −45° C. for 1 h
  2. extractionThe mixture was then extracted with ethyl acetate (×2)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried with Na2SO4
  5. customEvaporation

Sources & evidence

ORD record
ord-f4b04d9d77bd47daa6121070fc093ce0
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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