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

HRID 573056Notes

Reaction equation

HRID 573056 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-4edc66e13e2d4bfda439579d5ac33ecd
Source dataset
uspto-grants-2015_05
Patent number
US09029404B2

Reaction notes

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