Piperidine → 4-((R)-1-amino-2-methylpropyl)-N-(tetrahydro-2H-pyran-2-yloxy)benzamide

HRID 1049101Notes

Reaction equation

HRID 1049101 reaction equation
[CH3:1][CH:2]([CH3:38])[C@@H:3]([NH:20]C(=O)OCC1C2C=CC=CC=2C2C1=CC=CC=2)[C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:19])[NH:11][O:12][CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][O:14]2)=[CH:6][CH:5]=1.N1CCCCC1>C(O)C>[NH2:20][C@@H:3]([C:4]1[CH:5]=[CH:6][C:7]([C:10]([NH:11][O:12][CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][O:14]2)=[O:19])=[CH:8][CH:9]=1)[CH:2]([CH3:38])[CH3:1]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 86657280(9H-fluoren-9-yl)methyl (1R)-2-methyl-1-(4-(tetrahydro-2H-pyran-2-yloxycarbamoyl)phenyl)propylcarbamate

Product 1

HCID 866572794-((R)-1-amino-2-methylpropyl)-N-(tetrahydro-2H-pyran-2-yloxy)benzamideYield 41%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a 1-L round-bottom flask was added (9H-fluoren-9-yl)methyl (1R)-2-methyl-1-(4-(tetrahydro-2H-pyran-2-yloxycarbamoyl)phenyl)propylcarbamate (10.0 g, 0.0195 mol), ethanol (588 mL), and piperidine (51.7 mL). The solution was stirred at rt for 16 h, then concentrated to give a solid. Flash column chromatography gave 4-((R)-1-amino-2-methylpropyl)-N-(tetrahydro-2H-pyran-2-yloxy)benzamide (2.3 g, 41%). 1H NMR (CDCl3, 400 MHz) δ7.59 (d, J=8.0 Hz, 2H), 7.23 (d, J=8.0 Hz, 2H), 5.00 (m, 1H), 3.95 (m, 1H), 3.59 (m, 2H), 1.83 (m, 4H), 1.57 (m, 3H), 1.20 (m, 1H), J=6.8 Hz, 3H), 0.67 (t, J=6.8 Hz, 3H).

Workup

  1. concentrationconcentrated
  2. customto give a solid

Sources & evidence

ORD record
ord-04f294e8eda74fce8c5d481cc4dee63a
Source dataset
uspto-grants-2016_07
Patent number
US09382197B2

Reaction notes

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