Benzyl-4-(benzyloxymethoxy)-4-(2-fluoro-2-methylpropyl)piperidine-1-carboxylate → 4-(2-Fluoro-2-methylpropyl)piperidin-4-ol

HRID 514863Notes

Reaction equation

HRID 514863 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][C:14]([O:22]COCC2C=CC=CC=2)([CH2:17][C:18]([F:21])([CH3:20])[CH3:19])[CH2:13][CH2:12]1)=O)C1C=CC=CC=1>[Pd].CO>[F:21][C:18]([CH3:20])([CH3:19])[CH2:17][C:14]1([OH:22])[CH2:13][CH2:12][NH:11][CH2:16][CH2:15]1

Participants

4

Reactant 1

HCID 90418934Benzyl-4-(benzyloxymethoxy)-4-(2-fluoro-2-methylpropyl)piperidine-1-carboxylate

Product 1

HCID 904190284-(2-Fluoro-2-methylpropyl)piperidin-4-ol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a round bottom flask was added benzyl-4-(benzyloxymethoxy)-4-(2-fluoro-2-methylpropyl)piperidine-1-carboxylate (50 mg, 0.12 mmol), Pd/C (20 mg), and methanol (5 mL). The mixture was stirred at room temperature for 16 hrs under hydrogen atmosphere. The reaction mixture was filtered to get a solution, which was concentrated to give the desired product. The crude product was used directly for the next step. LC-MS: m/z 176.2 (M+H)+

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto get a solution, which
  3. concentrationwas concentrated

Sources & evidence

ORD record
ord-beb09356dd5543eebe5f3336e6cd2731
Source dataset
uspto-grants-2015_08
Patent number
US09108921B2

Reaction notes

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