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

HRID 629592Notes

Reaction equation

HRID 629592 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

A mixture of tert-butyl piperidin-4-ylcarbamate (45 g) and dihydro-2H-pyran-4(3H)-one (24.74 g) in dichloromethane (1000 mL) was treated with sodium triacetoxyborohydride (61.9 g), stirred at room temperature for 16 hours, washed with 1M sodium hydroxide and dried with anhydrous sodium sulfate, filtered and concentrated. The concentrate was flash column chromatographed on silica gel with 10-20% methanol/dichloromethane.

Workup

  1. washwashed with 1M sodium hydroxide
  2. dry with materialdried with anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customchromatographed on silica gel with 10-20% methanol/dichloromethane

Sources & evidence

ORD record
ord-bf8836a30afa45a8bb5b0c9ec3f3e699
Source dataset
uspto-grants-2016_04
Patent number
US09315488B2

Reaction notes

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