HCID 67969353, compound → tert-Butyl ((3S,5R)-5-methylpiperidin-3-yl)carbamate

HRID 924447Notes

Reaction equation

HRID 924447 reaction equation
C([N:8]1[CH2:13][C@H:12]([CH3:14])[CH2:11][C@H:10]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:9]1)C1C=CC=CC=1>CO.[Pd]>[CH3:14][C@H:12]1[CH2:13][NH:8][CH2:9][C@@H:10]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:11]1

Participants

4

Reactant 1

HCID 67969353HCID 67969353, compound

Product 1

HCID 57433105tert-Butyl ((3S,5R)-5-methylpiperidin-3-yl)carbamate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10 wt % Pd on carbon (120 mg, 0.11 mmol) was added to a solution of tert-butyl [(3S,5R)-1-benzyl-5-methylpiperidin-3-yl]carbamate (0.34 g, 1.1 mmol) in MeOH (15.0 mL). The mixture was stirred at room temperature under a hydrogen atmosphere (1 atm.) for 15 h. The reaction was filtered through a pad of diatomaceous earth (eluted with MeOH), and then concentrated under reduced pressure. The resulting crude product was used directly in the next step without further purification (0.21 g, 88%). LCMS calc. for C11H23N2O2 (M+H)+: m/z=215.2. found: 215.2. 1H NMR (CDCl3, 400 MHz) δ 4.33 (1H, m), 3.46 (1H, m), 3.25 (1H, m), 2.94 (1H, dd, J=3.6 and 12.8 Hz), 2.18-2.02 (3H, m), 1.60 (1H, m), 1.43 (9H, s), 0.85 (3H, d, J=6.8 Hz) ppm.

Workup

  1. filtrationThe reaction was filtered through a pad of diatomaceous earth (eluted with MeOH)
  2. concentrationconcentrated under reduced pressure
  3. customThe resulting crude product was used directly in the next step without further purification (0.21 g, 88%)

Sources & evidence

ORD record
ord-218b528b440f4e95955b05420d00b502
Source dataset
uspto-grants-2016_03
Patent number
US09278950B2

Reaction notes

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