Ethyl (3S,4R)-4-{[(benzyloxy)carbonyl]amino}-3-ethoxypiperidine-1-carboxylate → Ethyl (3S,4R)-4-amino-3-ethoxypiperidine-1-carboxylate

HRID 655760Notes

Reaction equation

HRID 655760 reaction equation
C(OC([NH:11][C@@H:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:14][C@@H:13]1[O:23][CH2:24][CH3:25])=O)C1C=CC=CC=1.[H][H]>CO.[Pd]>[NH2:11][C@@H:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:14][C@@H:13]1[O:23][CH2:24][CH3:25]

Participants

5

Reactant 2

HCID 58066116Ethyl (3S,4R)-4-{[(benzyloxy)carbonyl]amino}-3-ethoxypiperidine-1-carboxylate2×HCID 178418361HCID 178418361, compound

Product 1

HCID 54237477Ethyl (3S,4R)-4-amino-3-ethoxypiperidine-1-carboxylateYield 89.62%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Ethyl (3S,4R)-4-{[(benzyloxy)carbonyl]amino}-3-ethoxypiperidine-1-carboxylate (Intermediate 23, 2.4 g, 6.87 mmol) was dissolved in methanol (150 mL) and hydrogenated over 10% palladium on carbon (1.5 g) under 50 psi of hydrogen pressure for 2 h at room temperature. The reaction mixture was then filtered through a celite bed and the filtrate was concentrated under reduced pressure to yield 1.33 g (89.62%) of Ethyl (3S,4R)-4-amino-3-ethoxypiperidine-1-carboxylate as liquid.

Workup

  1. filtrationThe reaction mixture was then filtered through a celite bed
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-06ee2082ea1c45aaa6f426e301b7cda4
Source dataset
uspto-grants-2011_12
Patent number
US08071605B2

Reaction notes

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