Ethyl Acetate → HCID 11611666, compound

HRID 600751Notes

Reaction equation

HRID 600751 reaction equation
[F:1][C:2]([F:31])([F:30])[C:3]([CH2:18][C:19]1([CH3:29])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22][CH2:21][CH2:20]1)([OH:17])[CH:4]=[N:5][C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[CH:8]=[CH:9][C:10]([CH3:16])=[N:11]2.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C>C(O)(=O)C>[F:31][C:2]([F:1])([F:30])[C:3]([CH2:18][C:19]1([CH3:29])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22][CH2:21][CH2:20]1)([OH:17])[CH2:4][NH:5][C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[CH:8]=[CH:9][C:10]([CH3:16])=[N:11]2

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 24749260HCID 24749260, compound2×

Product 1

HCID 11611666HCID 11611666, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 1,1,1-trifluoro-3-[(2-methyl-5-quinolinyl)imino]-2-[(1-methyl-1,2,3,4-tetrahydro-1-naphthalenyl)methyl]-2-propanol (intermediate 8) (130 mg, 0.30 mmol) in glacial acetic acid (4 ml) stirred under nitrogen at 21° C., was added sodium triacetoxyborohydride (254 mg, 1.2 mmol) portionwise over 25 min and the solution was stirred for a further 4 h. The solution was then carefully added to a mixture of saturated aqueous sodium carbonate (50 ml) and ethyl acetate (30 ml) and stirred for 10 min, when effervescence had finished. The layers were separated and the aqueous layer re-extracted with ethyl acetate (30 ml) and the combined organic layers were washed with saturated sodium carbonate (15 ml), water (2×30 ml) and saturated brine (30 ml), dried over anhydrous sodium sulphate and evaporated. The crude product was purified on a 50 g silica cartridge using a Flashmaster 2 system with a 0-100% gradient of ethyl acetate in cyclohexane over 80 min to give the title compound (91.6 mg, 71%) as a mixture of diastereomers.

Workup

  1. stirringstirred for 10 min
  2. customThe layers were separated
  3. extractionthe aqueous layer re-extracted with ethyl acetate (30 ml)
  4. washthe combined organic layers were washed with saturated sodium carbonate (15 ml), water (2×30 ml) and saturated brine (30 ml)
  5. dry with materialdried over anhydrous sodium sulphate
  6. customevaporated
  7. customThe crude product was purified on a 50 g silica cartridge
  8. customover 80 min

Sources & evidence

ORD record
ord-c62872c292074ad098fecbc507e1919e
Source dataset
uspto-grants-2011_03
Patent number
US07902224B2

Reaction notes

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