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

HRID 1499488Notes

Reaction equation

HRID 1499488 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 residue 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 residue without further purification (0.21 g, 88%)

Sources & evidence

ORD record
ord-c5172ba018aa497fb8871377b2221405
Source dataset
uspto-grants-2015_12
Patent number
US09200004B2

Reaction notes

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