Methyl Ethyl Ketone → HCID 178505532, compound

HRID 2421272Notes

Reaction equation

HRID 2421272 reaction equation
[CH:1]1([C@@H:7]([C:9]2[NH:10][CH:11]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)[N:13]=2)[NH2:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:28][C:29](=O)[CH2:30][CH3:31].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO.O>[CH:1]1([C@@H:7]([C:9]2[NH:10][CH:11]=[C:12]([C:14]3[CH:15]=[CH:16][C:17]([F:20])=[CH:18][CH:19]=3)[N:13]=2)[NH:8][CH:28]2[CH2:31][CH2:30][CH2:29]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

7

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 178511760HCID 178511760, compound

Product 1

HCID 178505532HCID 178505532, compoundYield 12%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
23 °C

Procedure

A mixture containing (S)-cyclohexyl[4-(4-fluorophenyl)-1H-imidazol-2-yl]methanamine (prepared in Stage 5.2; 519 mg; 0.0015 mol), triethylamine (0.4 ml; 0.003 mol) and butanone (140 mg; 0.002 mol) in 10 ml of methanol is stirred for thirty minutes at 23° C. Sodium triacetoxyborohydride (630 mg; 0.003 mol) is then added. The reaction mixture is stirred for sixteen hours then poured into water. After extraction with ethyl acetate, the organic phase is washed with a saturated solution of sodium chloride then dried over magnesium sulphate. The solvent is evaporated off and the residue is purified on a silica column (eluent: CH2Cl2-MeOH mixture/95-05). A white-coloured powder is obtained with a yield of 12%. Melting point: 170-172° C.

Workup

  1. stirringThe reaction mixture is stirred for sixteen hours
  2. extractionAfter extraction with ethyl acetate
  3. washthe organic phase is washed with a saturated solution of sodium chloride
  4. dry with materialthen dried over magnesium sulphate
  5. customThe solvent is evaporated off
  6. customthe residue is purified on a silica column (eluent: CH2Cl2-MeOH mixture/95-05)
  7. customA white-coloured powder is obtained with a yield of 12%

Sources & evidence

ORD record
ord-9407549af8cd4ba9bbe05091973d5f14
Source dataset
uspto-grants-2011_06
Patent number
US07956075B2

Reaction notes

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