(R)-benzyl 3-(tert-butoxycarbonyl(methyl)amino)piperidine-1-carboxylate → tert-Butyl methyl((3R)-piperidin-3-yl)carbamate

HRID 875616Notes

Reaction equation

HRID 875616 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:25])[C@@H:9]1[CH2:14][CH2:13][CH2:12][N:11](C(OCC2C=CC=CC=2)=O)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.CCO.[Pd]>[CH3:25][N:8]([C@@H:9]1[CH2:14][CH2:13][CH2:12][NH:11][CH2:10]1)[C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 1

HCID 86652138(R)-benzyl 3-(tert-butoxycarbonyl(methyl)amino)piperidine-1-carboxylate

Product 1

HCID 28875356tert-Butyl methyl((3R)-piperidin-3-yl)carbamateYield 82%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

A solution of (R)-benzyl 3-(tert-butoxycarbonyl(methyl)amino)piperidine-1-carboxylate (4.00 g, 11.5 mmol) in methanol (10 mL) was slowly added to a suspension of 5% Pd on activated carbon (2.44 g, 1.15 mmol) in EtOH (20 mL). The reaction mixture was evacuated and back filled with N2 (3 cycles). The reaction vessel was then evacuated and back filled with H2 (3 cycles) using a H2 balloon. The mixture was stirred under H2 atmosphere for 1 hour and filtered through a pad of celite, washing with additional 10% MeOH/EtOAc (3×20 mL). The filtrate collected was concentrated in vacuo to provide (R)-tert-butyl methyl(piperidin-3-yl)carbamate (2.01 g, 82% yield) as an oil. LCMS (APCI+) m/z 215 (M+H)+.

Workup

  1. customThe reaction mixture was evacuated
  2. additionback filled with N2 (3 cycles)
  3. customThe reaction vessel was then evacuated
  4. additionback filled with H2 (3 cycles)
  5. filtrationfiltered through a pad of celite
  6. washwashing with additional 10% MeOH/EtOAc (3×20 mL)
  7. customThe filtrate collected
  8. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-f386c62b2c3c45c79c99a5e4f6a1098f
Source dataset
uspto-grants-2015_03
Patent number
US08981085B2

Reaction notes

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