Cyclopropanecarboxaldehyde → 4-((3,5-Bis(trifluoromethyl)benzyloxy)methyl)-1-(cyclopropylmethyl)-4-phenylazepane

HRID 11222

반응식

HRID 11222 반응식
[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.[CH:31]1([CH:34]=O)[CH2:33][CH2:32]1.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]([CH2:34][CH:31]2[CH2:33][CH2:32]2)[CH2:11][CH2:10]1

참가 물질

6

반응물 3

HCID 123114CyclopropanecarboxaldehydeHCID 5003444Sodium cyanoborohydrideHCID 116261604-((3,5-Bis(trifluoromethyl)benzyloxy)methyl)-4-phenylazepane

생성물 1

HCID 219731184-((3,5-Bis(trifluoromethyl)benzyloxy)methyl)-1-(cyclopropylmethyl)-4-phenylazepane수율 41.5%

시약·촉매·용매 2

HCID 6422Trifluoroacetic acid촉매HCID 887Methanol용매

실험 절차

Mixture of isomer A of 4-((3,5-bis(trifluoromethyl)benzyloxy)methyl)-4-phenylazepane (3 mg) and cyclopropanecarbaldehyde (1.4 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 room temperature for overnight and concentrated under vacuum. Then saturated sodium bicarbonate 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 (1.4 mg, 41% yield).

후처리

  1. stirringThe mixture was stirred at room temperature for overnight
  2. concentrationconcentrated under vacuum
  3. additionThen saturated sodium bicarbonate 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

출처 및 근거

ORD 기록
ord-55ba5bde656147629274f122dc38c215
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07098203B2

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