Methanol → tert-Butyl 3-{4-cyclopropyl-5-[3-(2,2-dimethylpropyl)cyclobutyl]isoxazol-3-yl]-6-hydroxyhexanoate

HRID 1912078Notes

Reaction equation

HRID 1912078 reaction equation
C([O:8][CH2:9][CH2:10][CH2:11][CH:12]([C:21]1[C:25]([CH:26]2[CH2:28][CH2:27]2)=[C:24]([CH:29]2[CH2:32][CH:31]([CH2:33][C:34]([CH3:37])([CH3:36])[CH3:35])[CH2:30]2)[O:23][N:22]=1)[CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])C1C=CC=CC=1.CO>[Pd].O1CCCC1>[CH:26]1([C:25]2[C:21]([CH:12]([CH2:11][CH2:10][CH2:9][OH:8])[CH2:13][C:14]([O:16][C:17]([CH3:19])([CH3:18])[CH3:20])=[O:15])=[N:22][O:23][C:24]=2[CH:29]2[CH2:30][CH:31]([CH2:33][C:34]([CH3:37])([CH3:36])[CH3:35])[CH2:32]2)[CH2:27][CH2:28]1

Participants

5

Reactant 2

HCID 887MethanolHCID 71127331tert-Butyl 6-benzyloxy-3-[4-cyclopropyl-5-[3-(2,2-dimethylpropyl)cyclobutyl]isoxazol-3-yl]hexanoate

Product 1

HCID 71127332tert-Butyl 3-{4-cyclopropyl-5-[3-(2,2-dimethylpropyl)cyclobutyl]isoxazol-3-yl]-6-hydroxyhexanoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl 6-benzyloxy-3-{4-cyclopropyl-5-[3-(2,2-dimethylpropyl)cyclobutyl]isoxazol-3-yl]hexanoate (980 mg), methanol (10 mL) and tetrahydrofuran (3 mL) were mixed. To the mixture was added 7.5 w/w % palladium on activated carbon (200 mg). The mixture was stirred at RT under hydrogen atmosphere (1 atm) for 5 hr. The catalyst was freshened up, and the mixture was stirred at RT under hydrogen atmosphere (1 atm) overnight. The 7.5 w/w % palladium on activated carbon was filtered off and the filtrate was concentrated in vacuo.

Workup

  1. stirringthe mixture was stirred at RT under hydrogen atmosphere (1 atm) overnight
  2. filtrationThe 7.5 w/w % palladium on activated carbon was filtered off
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-2fa4d51256e84ab791e9e52f57e2995f
Source dataset
uspto-grants-2013_12
Patent number
US08604069B2

Reaction notes

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