HCID 86714763, compound → HCID 86714764, compound

HRID 1055092Notes

Reaction equation

HRID 1055092 reaction equation
C([N:8]1[CH:12]([C:13]2([CH3:17])[CH2:16][CH2:15][CH2:14]2)[CH2:11][C:10](=[O:18])[O:9]1)C1C=CC=CC=1.[H][H]>CO.[OH-].[Pd+2].[OH-]>[NH2:8][CH:12]([C:13]1([CH3:17])[CH2:16][CH2:15][CH2:14]1)[CH2:11][C:10]([OH:18])=[O:9]

Participants

5

Reactant 2

HCID 86714763HCID 86714763, compound2×HCID 178418361HCID 178418361, compound

Product 1

HCID 86714764HCID 86714764, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A solution of racemic 2-benzyl-3-(1-methylcyclobutyl)isoxazolidin-5-one, 115a, (0.18 g, 1.28 mmol) in MeOH (2.9 mL) was shaken overnight under 50 psi hydrogen in the presence of 50 mg palladium hydroxide catalyst. The mixture was filtered through Celite and the volatiles were removed under reduced pressure to afford the desired product that was used without further purification: 1H NMR (400 MHz, MeOD) δ 3.42 (dd, J=11.0, 1.9 Hz, 1H), 2.26 (ddd, J=27.8, 16.7, 6.5 Hz, 2H), 1.86 (dddd, J=36.9, 26.3, 11.2, 7.6 Hz, 6H), 1.18 (s, 3H).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customthe volatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-8f4f3d6aea5747ffb2a108d13a69335e
Source dataset
uspto-grants-2016_07
Patent number
US09394302B2

Reaction notes

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