Ethyl formate → 1,1-Dimethylethyl 3-(formylamino)-1-piperidinecarboxylate

HRID 1898972Notes

Reaction equation

HRID 1898972 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1.[CH:15](OCC)=[O:16]>>[C:11]([O:10][C:8]([N:4]1[CH2:5][CH2:6][CH2:7][CH:2]([NH:1][CH:15]=[O:16])[CH2:3]1)=[O:9])([CH3:14])([CH3:13])[CH3:12]

Participants

3

Reactant 2

HCID 8025Ethyl formateHCID 5458091-BOC-3-Aminopiperidine

Product 1

HCID 5812961,1-Dimethylethyl 3-(formylamino)-1-piperidinecarboxylate

Procedure

The title compound of Example 4 (10.1 g, 50.5 mmol) was dissolved in ethyl formate (50 mL) and the solution was refluxed overnight when TLC (solvent system A) showed the reaction to be complete. The solvent was evaporated in vacuo and the residue was dried under high vacuum to give the product (11.5 g, quantitative) as a colorless oil: 1H-NMR (CDCl3) ∂8.16. (s, 1H), 6.03 (20%), 5.77 (80%) (br s, 1H), 4.06 (m, 1H), 3.22-3.58 (complex m, 4H), 1.20-1.89 (complex m, 4H), 1.46 (s, 9H). CIMS (MH+ calcd for C11H20N2O3): 229. Found (MH+): 229; HRMS (M+ calcd for C11H20N2O3): 228. 1474. Found (M+): 228. 1469.

Workup

  1. temperaturethe solution was refluxed overnight when TLC (solvent system A)
  2. customthe reaction
  3. customThe solvent was evaporated in vacuo
  4. customthe residue was dried under high vacuum
  5. customto give the product (11.5 g, quantitative) as a colorless oil

Sources & evidence

ORD record
ord-db36be5dfebe402ba7964f7bcae81394
Source dataset
uspto-grants-1996_11
Patent number
US05571832

Reaction notes

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