Formic Acid → HCID 19706115, compound

HRID 915888Notes

Reaction equation

HRID 915888 reaction equation
C(Cl)(Cl)Cl.[NH:5]1[CH2:10][CH2:9][CH:8]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:7][CH2:6]1.[C:19](OC(=O)C)(=[O:21])C.C(O)=O>O>[CH:19]([N:5]1[CH2:6][CH2:7][CH:8]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:15])([CH3:17])[CH3:16])[CH2:9][CH2:10]1)=[O:21]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 6212ChloroformHCID 7918Acetic AnhydrideHCID 7238334-(N-Boc-amino)piperidine

Product 1

HCID 19706115HCID 19706115, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A chloroform solution of 2.0 g of tert-butyl piperidin-4-ylcarbamate was added to a mixed solution of 4.7 ml of acetic anhydride and 1.9 ml of formic acid, and the reaction mixture was stirred at room temperature for 15 hours. Water was added to the reaction mixture, and this was extracted with EtOAc. The organic layer was washed with 1 M hydrochloric acid, aqueous saturated sodium hydrogencarbonate and brine. This was dried with anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The resulting residue was purified with silica gel column chromatography (eluent: chloroform/MeOH=50/1) to obtain 1.7 g of tert-butyl (1-formylpiperidin-4-yl)carbamate.

Workup

  1. extractionthis was extracted with EtOAc
  2. washThe organic layer was washed with 1 M hydrochloric acid, aqueous saturated sodium hydrogencarbonate and brine
  3. dry with materialThis was dried with anhydrous magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe resulting residue was purified with silica gel column chromatography (eluent: chloroform/MeOH=50/1)

Sources & evidence

ORD record
ord-ae0e9eddbf06415081e6a521a5af8885
Source dataset
uspto-grants-2007_09
Patent number
US07268150B2

Reaction notes

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