Borane → HCID 71257562, compound

HRID 2200815Notes

Reaction equation

HRID 2200815 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([O:11][C:12]3[CH:13]=[C:14]([CH:18]=[C:19]([C:21]([F:24])([F:23])[F:22])[N:20]=3)[C:15](O)=[O:16])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.B>O1CCCC1>[O:4]1[C:5]2([CH2:6][CH2:7][CH:8]([O:11][C:12]3[CH:13]=[C:14]([CH2:15][OH:16])[CH:18]=[C:19]([C:21]([F:23])([F:22])[F:24])[N:20]=3)[CH2:9][CH2:10]2)[O:1][CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 6331BoraneHCID 71257376HCID 71257376, compound

Product 1

HCID 71257562HCID 71257562, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

2-(1,4-Dioxaspiro[4.5]dec-8-yloxy)-6-(trifluoromethyl)isonicotinic acid (490.0 mg, 1.411 mmol) was dissolved in tetrahydrofuran (17.5 mL) and cooled to 0° C. 1.0 M Borane in THF (4.23 mL, 4.23 mmol) was then added and stirred at 0° C. for 10 min and at 25° C. for 16 hours when LCMS analysis showed the absence of starting material. The reaction was quenched with 1N NaOH and water, and extracted with EtOAc. The EtOAc extract was evaporated in vacuo and the residue was used in the next reaction without further purification. MS (ES): 334 (M+1).

Workup

  1. customThe reaction was quenched with 1N NaOH and water
  2. extractionextracted with EtOAc
  3. extractionThe EtOAc extract
  4. customwas evaporated in vacuo
  5. customthe residue was used in the next reaction without further purification

Sources & evidence

ORD record
ord-06ec6e8c42404979ae4553ffa2e16bed
Source dataset
uspto-grants-2016_06
Patent number
US09359358B2

Reaction notes

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