Water → tert-Butyl 3-azidopiperidine-1-carboxylate

HRID 341767Notes

Reaction equation

HRID 341767 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10](OS(C)(=O)=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N-:19]=[N+:20]=[N-:21].[Na+].O>CN(C=O)C>[N:19]([CH:10]1[CH2:11][CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9]1)=[N+:20]=[N-:21]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 568122N-Boc-3-mesyloxypiperidine

Product 1

HCID 547722tert-Butyl 3-azidopiperidine-1-carboxylateYield 98.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of the title compound of Example 2 (45.1 g, 205 mmol) and NaN3 (39.9 g, 614 mmol, 3.0 eq) in DMF (200 mL) was heated and stirred at 70° C. for 48 h when TLC (solvent system C) indicated the reaction to be complete. The reaction mixture was cooled to rt and poured into cold water (200 mL). The aqueous mixture was extracted with Et2O (500 mL) and the organic extract was back-washed with water (2×100 mL), dried (Na2SO4) and the solvent was evaporated in vacuo to afford the title compound (45.5 g, 98%) as a colorless oil: 1H-NMR (CDCl3) ∂ 3.66-3.80 (m, 1H), 3.57 (m, 1H), 3.45 (m, Japp =4.0 Hz, 1H), 3.12 (m, 2H), 1.90-2.05 (m, 2H), 1.69-1.83 (m, 2H), 1.47 (s, 9H).

Workup

  1. temperaturewas heated
  2. customthe reaction
  3. temperatureThe reaction mixture was cooled to rt
  4. extractionThe aqueous mixture was extracted with Et2O (500 mL)
  5. extractionthe organic extract
  6. washwas back-washed with water (2×100 mL)
  7. dry with materialdried (Na2SO4)
  8. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-b19525a8a8244751b336250d63eb4920
Source dataset
uspto-grants-1999_01
Patent number
US05856318

Reaction notes

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