(2R,3R)-benzyl 3-(tert-butoxycarbonylamino)-2-methylpiperidine-1-carboxylate → tert-butyl N-[(2R,3R)-2-methylpiperidin-3-yl]carbamate

HRID 1050559Notes

Reaction equation

HRID 1050559 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][N:11](C(OCC2C=CC=CC=2)=O)[C@@H:10]1[CH3:25])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CC(O)C.[Pd]>[CH3:25][C@@H:10]1[C@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:14][CH2:13][CH2:12][NH:11]1

Participants

4

Reactant 1

HCID 59223903(2R,3R)-benzyl 3-(tert-butoxycarbonylamino)-2-methylpiperidine-1-carboxylate

Product 1

HCID 40152174tert-butyl N-[(2R,3R)-2-methylpiperidin-3-yl]carbamateYield 104.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

(2R,3R)-Benzyl 3-(tert-butoxycarbonylamino)-2-methylpiperidine-1-carboxylate (308) (1.7 g, 4.9 mmol) was dissolved in IPA (20 mL). 10% Pd/C (1 g) was added and the mixture was hydrogenated on a Parr shaker at 50 psi pressure for 12 hours. The reaction mixture was filtered through celite, and the solvent was removed under reduced pressure to give tert-butyl (2R,3R)-2-methylpiperidin-3-ylcarbamate (310), (1.1 g, 5.1 mmol, 100% yield).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-af9cce8e479d4a729597a563d48d32f6
Source dataset
uspto-grants-2016_07
Patent number
US09382246B2

Reaction notes

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