Water → N-(tert-butoxycarbonyl)piperidine

HRID 1817835Notes

Reaction equation

HRID 1817835 reaction equation
[H-].[Na+].[C:3]([N:10]([CH2:14][CH2:15]Cl)[CH2:11][CH2:12]Cl)([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].O.[CH3:18]N(C)C=O>>[C:3]([N:10]1[CH2:14][CH2:15][CH2:18][CH2:12][CH2:11]1)([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4]

Participants

5

Reactant 4

HCID 962WaterHCID 6228Dimethylformamide3×HCID 24758Sodium hydrideHCID 11230235N-BOC-N,N-Bis(2-chloroethyl)amine

Product 1

HCID 7010304N-(tert-butoxycarbonyl)piperidine

Procedure

Intermediate 1 (2.5 g, 8.3 mmol) was dissolved in dimethylformamide (6 mL), and added dropwise to a suspension of 60% sodium hydride in mineral oil (635 mg 16.6 mmol) in dimethylformamide (6 mL). When the effervescence had ceased the solution was treated with a solution of N—Boc-bis-(2-chloroethyl)amine (3.75 g, 12 mmol) in dimethylformamide (3 mL). The mixture was stirred at r.t. for 36 hrs. Water (800 mL) was added and the solution washed with ethyl acetate (2×500 mL). The organic phase washed with brine (500 mL), dried (MgSO4) and evaporated. The clear oil obtained was purified by column chromatography on silica gel eluting with 5-20% ethyl acetate in hexanes. The oil obtained was then further purified by column chromatography on silica gel eluting with dichloromethane to give the Boc-piperidine. 1H NMR (CDCl3) 7.41-7.34 (4H, m), 7.13-7.05 (2H, m), 6.91-6.83 (1H, m), 4.25-4.15 (2H, m), 2.72-2.56 (4H, m), 2.34-2.23 (2H, m) and 1.43 (9H, s)

Workup

  1. washthe solution washed with ethyl acetate (2×500 mL)
  2. washThe organic phase washed with brine (500 mL)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe clear oil obtained
  6. customwas purified by column chromatography on silica gel eluting with 5-20% ethyl acetate in hexanes
  7. customThe oil obtained
  8. customwas then further purified by column chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-042e6450fe9b4a179343772049e3bd7e
Source dataset
uspto-grants-2009_10
Patent number
US07598386B2

Reaction notes

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