Hydrochloric Acid → HCID 86704397, compound

HRID 1748158Notes

Reaction equation

HRID 1748158 reaction equation
[CH:1]1([C:4]2[O:8][N:7]=[C:6]([C@@H:9]3[CH2:11][C@H:10]3[C:12]([F:15])([F:14])[F:13])[C:5]=2[C:16](OC)=[O:17])[CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>C1COCC1>[CH:1]1([C:4]2[O:8][N:7]=[C:6]([C@@H:9]3[CH2:11][C@H:10]3[C:12]([F:14])([F:13])[F:15])[C:5]=2[CH2:16][OH:17])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 86704398HCID 86704398, compound

Product 1

HCID 86704397HCID 86704397, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A cold (0°C.) solution of methyl 5-cyclopropyl-3-((trans)-2-(trifluoromethyl)cyclopropyl)isoxazole-4-carboxylate (193 mg, 0.7 mmol) in THF (2.3 mL) was treated with the dropwise addition of lithium aluminum hydride (1.4 mL, 1M solution in THF). Afte(2 hr of stirring, the reaction was cooled to 0°C. and treated with the dropwise addition of 1N HCl (aq.) until a solution persisted. The reaction was then extracted with EtOAc. The organic phase was dried (MgSO4), filtered, concentrated, and chromatographed (SiO2, linear gradient, 0-80%, EtOAc in hexanes) to give the title compound. 1H NMR (400 MHz, CDCl3) δ 4.63 (d, J=4.5 Hz, 2H), 2.31 (m, 1H), 2.14 (m, 1H), 2.01 (m, 1H), 1.67 (dd, J=5.1, 4.9 Hz, 1H), 1.42 (m, 2H), 1.10 (m, 2H), 1.05 (m, 2H), MS m/z 248.1 (M+1).

Workup

  1. extractionThe reaction was then extracted with EtOAc
  2. dry with materialThe organic phase was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customchromatographed (SiO2, linear gradient, 0-80%, EtOAc in hexanes)

Sources & evidence

ORD record
ord-3053fa49f194473797ac0e4d36ff3a02
Source dataset
uspto-grants-2015_10
Patent number
US09150568B2

Reaction notes

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