(R)-6-(benzyloxycarbonylamino)-3-(tert-butoxycarbonylamino)-2-hexanone → (R)-tert-butyl 2-methylpiperidin-3-ylcarbamate

HRID 1050557Notes

Reaction equation

HRID 1050557 reaction equation
C(OC([NH:11][CH2:12][CH2:13][CH2:14][C@@H:15]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:16](=O)[CH3:17])=O)C1C=CC=CC=1>CC(O)C.[Pd]>[CH3:17][C@@H:16]1[CH:15]([NH:19][C:20](=[O:21])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:14][CH2:13][CH2:12][NH:11]1

Participants

4

Reactant 1

HCID 98005910(R)-6-(benzyloxycarbonylamino)-3-(tert-butoxycarbonylamino)-2-hexanone

Product 1

HCID 118114667(R)-tert-butyl 2-methylpiperidin-3-ylcarbamateYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

(R)-6-(Benzyloxycarbonylamino)-3-(tert-butoxycarbonylamino)-2-hexanone (306) (14.3 g, 39.3 mmol) was divided in 2 equal batches and each batch was dissolved in IPA (70 mL), combined with 10% Pd/C (5.5 g), and hydrogenated on a Parr shaker at 50 psi pressure for 12 hours. The batches were combined, filtered through celite and concentrated in vacuo to give (R)-tert-butyl 2-methylpiperidin-3-ylcarbamate (307), (8.2 g, 38 mmol, 97% yield) as a clear oil.

Workup

  1. filtrationfiltered through celite and
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9a8c1a63f1e64868b4bf4e7f390e44d8
Source dataset
uspto-grants-2016_07
Patent number
US09382246B2

Reaction notes

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