Tetrahydro-4H-pyran-4-one → tert-butyl N-[1-(oxan-4-yl)piperidin-4-yl]carbamate

HRID 574762Notes

Reaction equation

HRID 574762 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:3][CH2:2]1.[O:15]1[CH2:20][CH2:19][C:18](=O)[CH2:17][CH2:16]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[O:15]1[CH2:20][CH2:19][CH:18]([N:1]2[CH2:2][CH2:3][CH:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:13])[CH3:12])[CH2:5][CH2:6]2)[CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 121599Tetrahydro-4H-pyran-4-oneHCID 7238334-(N-Boc-amino)piperidineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 45792109tert-butyl N-[1-(oxan-4-yl)piperidin-4-yl]carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tert-butyl piperidin-4-ylcarbamate (45.00 g, 225 mmol) and dihydro-2H-pyran-4(3H)-one (24.74 g, 247 mmol) were added to dichloromethane (1000 mL). Sodium triacetoxyborohydride (61.90 g, 292 mmol) was added, and the solution was stirred at room temperature for 16 hours. The solution was extracted with 1M sodium hydroxide and dried over anhydrous sodium sulfate. The solution was filtered and concentrated and purified by flash column chromatography on silica gel with 10% methanol (in dichloromethane) increasing to 20% methanol (in dichloromethane).

Workup

  1. extractionThe solution was extracted with 1M sodium hydroxide
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationThe solution was filtered
  4. concentrationconcentrated
  5. custompurified by flash column chromatography on silica gel with 10% methanol (in dichloromethane)
  6. temperatureincreasing to 20% methanol (in dichloromethane)

Sources & evidence

ORD record
ord-0000bc7bfcdc4a1d93c74d3f4c9336b4
Source dataset
uspto-grants-2015_05
Patent number
US09034875B2

Reaction notes

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