Acetone → HCID 21973119, compound

HRID 11223

Reaction equation

HRID 11223 reaction equation
[F:1][C:2]([F:30])([F:29])[C:3]1[CH:4]=[C:5]([CH:22]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:24]=1)[CH2:6][O:7][CH2:8][C:9]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:15][CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.[CH3:31][C:32]([CH3:34])=O.C([BH3-])#N.[Na+]>CO.FC(F)(F)C(O)=O>[F:30][C:2]([F:29])([F:1])[C:3]1[CH:4]=[C:5]([CH:22]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:24]=1)[CH2:6][O:7][CH2:8][C:9]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:15][CH2:14][CH2:13][N:12]([CH:32]([CH3:34])[CH3:31])[CH2:11][CH2:10]1

Participants

6

Reactant 3

HCID 180AcetoneHCID 5003444Sodium cyanoborohydrideHCID 116261604-((3,5-Bis(trifluoromethyl)benzyloxy)methyl)-4-phenylazepane

Product 1

HCID 21973119HCID 21973119, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidCatalystHCID 887MethanolSolvent

Procedure

Mixture of isomer A of 4-((3,5-bis(trifluoromethyl)benzyloxy)methyl)-4-phenylazepane (3 mg) and acetone (1.2 mg) in methanol (0.15 mL) was stirred at room temperature for 0.5 hr, then sodium cyanoborohydride (1.0 M solution in THF, 0.02 mL) was added followed by 1 drop of trifluoroacetic acid. The mixture was stirred at 65° C. for overnight and concentrated under vacuum. Then saturated sodium bicarbonate solution and dichloromethane was added to the mixture and the organic layer was separated. The aqueous layer was extracted with dichloromethane 2 times and the combined organic layers were dried over magnesium sulfate, filtered and concentrated under vacuum to give the product as a clear sticky oil (2.5 mg, 76% yield).

Workup

  1. stirringThe mixture was stirred at 65° C. for overnight
  2. concentrationconcentrated under vacuum
  3. additionThen saturated sodium bicarbonate solution and dichloromethane was added to the mixture
  4. customthe organic layer was separated
  5. extractionThe aqueous layer was extracted with dichloromethane 2 times
  6. dry with materialthe combined organic layers were dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-c9a402b306ff49baa560b3a2cd76a8ad
Source dataset
uspto-grants-2006_08
Patent number
US07098203B2

Linked notes

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