Acetone → HCID 21973119、化合物

HRID 11223

反応式

HRID 11223 の反応式
[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

参加物

6

反応物 3

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

生成物 1

HCID 21973119HCID 21973119、化合物収率 76%

試薬・触媒・溶媒 2

HCID 6422Trifluoroacetic acid触媒HCID 887Methanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-c9a402b306ff49baa560b3a2cd76a8ad
出典データセット
uspto-grants-2006_08
特許番号
US07098203B2

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