Acetic Acid → HCID 57809903, compound

HRID 2105984Notes

Reaction equation

HRID 2105984 reaction equation
[N:1]1([CH2:11][C:12]([OH:30])([CH2:17][C:18]([C:21]2[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=2[O:28][CH3:29])([CH3:20])[CH3:19])[C:13]([F:16])([F:15])[F:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][CH2:3][CH2:2]1.C=O.[C:33]([BH3-])#N.[Na+].C(O)(=O)C>C(#N)C>[F:16][C:13]([F:14])([F:15])[C:12]([CH2:11][N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([CH3:33])[CH2:3][CH2:2]1)([OH:30])[CH2:17][C:18]([C:21]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=1[O:28][CH3:29])([CH3:20])[CH3:19]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 57809838HCID 57809838, compound

Product 1

HCID 57809903HCID 57809903, compoundYield 86.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-(3,4-dihydro-2H-quinoxalin-1-ylmethyl)-1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methylpentan-2-ol (Example 4) (18.6 mg) in acetonitrile (3 mL) was added formaldehyde solution (37% w/w aqueous, 300 μL) followed by sodium cyanoborohydride (13.8 mg). After 30 minutes at room temperature, acetic acid (50.4 μL) was added. The resulting mixture was stirred for 3 hours, quenched with saturated aqueous sodium bicarbonate solution and extracted three times with methylene chloride. The combined organic phases were dried over sodium sulfate, filtered, and the volatiles removed in vacuo. The residue was purified by preparative TLC (eluted with 25% EtOAc-hexanes) to give the title compound as a pale yellow oil (16.6 mg).

Workup

  1. customquenched with saturated aqueous sodium bicarbonate solution
  2. extractionextracted three times with methylene chloride
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. filtrationfiltered
  5. customthe volatiles removed in vacuo
  6. customThe residue was purified by preparative TLC (eluted with 25% EtOAc-hexanes)

Sources & evidence

ORD record
ord-6f3ef2ab16474cf4a527f25fcb4042f9
Source dataset
uspto-grants-2009_08
Patent number
US07579469B2

Reaction notes

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