Diisopropylethylamine → HCID 178484845, 화합물

HRID 1063621

반응식

HRID 1063621 반응식
[CH3:1][NH:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([OH:9])[CH2:5][CH2:4]1.C(N(CC)C(C)C)(C)C.[F:19][C:20]([F:32])([F:31])[C:21]1[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1>C(Cl)Cl>[OH:9][C@H:6]1[CH2:7][CH2:8][C@H:3]([N:2]([CH3:1])[S:27]([C:24]2[CH:23]=[CH:22][C:21]([C:20]([F:19])([F:31])[F:32])=[CH:26][CH:25]=2)(=[O:29])=[O:28])[CH2:4][CH2:5]1

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 27773994-(Trifluoromethyl)benzenesulfonyl chlorideHCID 178484843HCID 178484843, 화합물

생성물 1

HCID 178484845HCID 178484845, 화합물수율 77%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To 3 g (23.2 mmol) of trans-4-methylamino-cyclohexanol in 120 mL of CH2Cl2 were added 4.2 mL (24.4 mmol, 1.05 eq) of N,N-diisopropylethylamine followed by 5.96 g (24.4 mmol, 1.05 eq) of 4-(trifluoromethyl)-benzenesulfonyl chloride in 50 mL of CH2Cl2. The mixture was stirred at RT over night and the organic phase was extracted with 1M KHSO4, followed by 5% NaHCO3. The combined organic phases were washed with brine, dried over Na2SO4 and evaporated. Column chromatography on silica gel with n-hexane:EtOAc 1:1 as eluent yielded 6.0 g (77%) of trans-N-(4-hydroxy-cyclohexyl)-N-methyl-4-trifluoromethyl-benzenesulfonamide as off-white solid, MS: 338 (MH+).

후처리

  1. extractionthe organic phase was extracted with 1M KHSO4
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated

출처 및 근거

ORD 기록
ord-ef16aeb14d6847a4afcdd8483c2f5d7a
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06965048B2

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