HCID 66858871, compound → HCID 66858638, compound

HRID 2179761Notes

Reaction equation

HRID 2179761 reaction equation
C(OC([NH:11][C@H:12]1[CH2:15][C@@H:14]([C:16]([N:18]2[CH2:23][CH2:22][CH:21]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:20][CH2:19]2)=[O:17])[C:13]1([CH3:30])[CH3:29])=O)C1C=CC=CC=1>C(OCC)(=O)C.[Pd]>[NH2:11][C@H:12]1[CH2:15][C@@H:14]([C:16]([N:18]2[CH2:19][CH2:20][CH:21]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:22][CH2:23]2)=[O:17])[C:13]1([CH3:29])[CH3:30]

Participants

4

Reactant 1

HCID 66858871HCID 66858871, compound

Product 1

HCID 66858638HCID 66858638, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of ethyl 1-((1R,3S)-3-(benzyloxycarbonylamino)-2,2-dimethylcyclobutanecarbonyl)piperidine-4-carboxylate (step 1, 1.30 g) in ethyl acetate (50 ml), Pd/C (100 mg) was added carefully under argon atmosphere. Then the reaction mixture was stirred for overnight under hydrogen conditions. After completion of the reaction (monitored by TLC), diluted with ethyl acetate, filtered on celite, washed with ethyl acetate. The combined organic extracts were concentrated under reduced pressure to give crude product which was preceded for next step without further purification and analysis.

Workup

  1. customAfter completion of the reaction (monitored by TLC)
  2. filtrationfiltered on celite
  3. washwashed with ethyl acetate
  4. concentrationThe combined organic extracts were concentrated under reduced pressure
  5. customto give crude product which
  6. customwas preceded for next step without further purification and analysis

Sources & evidence

ORD record
ord-4a1c946a3d884c65bb08f2d773a85748
Source dataset
uspto-grants-2015_06
Patent number
US09067966B2

Reaction notes

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