HCID 86714763, compound → HCID 86714764, compound

HRID 2171887Notes

Reaction equation

HRID 2171887 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-2ff93e4a9b6d40e9a88d5a0d6b42a8f1
Source dataset
uspto-grants-2015_06
Patent number
US09051319B2

Reaction notes

Loading…