Tert-butyl 4-(4-ethoxy-4-oxobutyl)piperidine-1-carboxylate → 4-Piperidinebutanoic acid, ethyl ester

HRID 2215521Notes

Reaction equation

HRID 2215521 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][CH2:7][CH2:8][CH:9]1[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH2:10]1)=[O:5])[CH3:2]>FC(F)(F)C(O)=O>[NH:12]1[CH2:13][CH2:14][CH:9]([CH2:8][CH2:7][CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:10][CH2:11]1

Participants

3

Reactant 1

HCID 10334920Tert-butyl 4-(4-ethoxy-4-oxobutyl)piperidine-1-carboxylate

Product 1

HCID 106318484-Piperidinebutanoic acid, ethyl esterYield 144.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl 4-(3-ethoxycarbonylpropyl)piperidine-1-carboxylate (1.2 g, 4.0 mmol, Production example 43-1) was dissolved in trifluoroacetic acid (30 ml), and the reaction mixture was stirred at room temperature for 20 minutes. This was concentrated under reduced pressure, and was further azeotropically distilled with toluene. The obtained residue was partitioned between ethyl acetate and a saturated aqueous solution of sodium hydrogencarbonate. The organic layer was dried over anhydrous magnesium sulfate. In addition, the aqueous layer was concentrated under reduced pressure to dryness; the obtained solid was suspended in tetrahydrofuran; insoluble portion were filtered off, and this solution was added to the previously obtained organic layer. This was purified by silica gel column chromatography (Fuji Silysia NH, hexane-ethyl acetate-methanol system) to yield the title compound (1.15 g, quantitative) as a yellow oil.

Workup

  1. concentrationThis was concentrated under reduced pressure
  2. distillationwas further azeotropically distilled with toluene
  3. customThe obtained residue was partitioned between ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationIn addition, the aqueous layer was concentrated under reduced pressure to dryness
  6. filtrationinsoluble portion were filtered off
  7. additionthis solution was added to the previously obtained organic layer
  8. customThis was purified by silica gel column chromatography (Fuji Silysia NH, hexane-ethyl acetate-methanol system)

Sources & evidence

ORD record
ord-5efd9871eae54a94b038de323a795e6d
Source dataset
uspto-grants-2006_09
Patent number
US07109219B2

Reaction notes

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