Triethylamine → 4-{2-[1-(Propane-2-sulfonyl)-piperidin-3-yloxy]-phenyl}-piperazine-1-carboxylic acid tert-butyl ester

HRID 456459노트

반응식

HRID 456459 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH:21]2[CH2:26][CH2:25][CH2:24][N:23](C(OCC3C=CC=CC=3)=O)[CH2:22]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H].C(N(CC)CC)C.[CH:46]([S:49](Cl)(=[O:51])=[O:50])([CH3:48])[CH3:47]>CO.[Pd].C(OCC)(=O)C.C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH:21]2[CH2:26][CH2:25][CH2:24][N:23]([S:49]([CH:46]([CH3:48])[CH3:47])(=[O:51])=[O:50])[CH2:22]2)[CH2:12][CH2:13]1)=[O:7])([CH3:3])([CH3:2])[CH3:4]

참가 물질

9

반응물 4

HCID 8471Triethylamine2회HCID 824082-Propanesulfonyl chlorideHCID 694231604-[2-(1-Benzyloxycarbonyl-piperidin-3-yloxy)-phenyl]-piperazine-1-carboxylic acid tert-butyl esterHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 694200544-{2-[1-(Propane-2-sulfonyl)-piperidin-3-yloxy]-phenyl}-piperazine-1-carboxylic acid tert-butyl ester수율 80%

시약·촉매·용매 4

HCID 23938Palladium촉매HCID 887Methanol용매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매2회

실험 절차

4-[2-(1-Benzyloxycarbonyl-piperidin-3-yloxy)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester (2.5 g, 4.7 mmol) was dissolved in methanol (20 mL). Palladium on carbon (50% water, 2.1 g) was added. A hydrogen atmosphere was established using balloons, and the mixture was stirred at r.t. for about 4 hours. The catalyst was removed by filtration with ethyl acetate through a bed of celite. The compound was isolated by running a silica gel plug with a gradient of 100% ethyl acetate (200 mL) to triethylamine in ethyl acetate (10%). The isolated product (0.382 g, 0.96 mmol) was dissolved in methylene chloride (10 mL) at 0° C., and triethylamine (0.4 mL, 2.9 mmol) was added. Isopropylsulfonyl chloride (0.13 mL, 1.15 mmol) was added dropwise, and the mixture was warmed to r.t. for about 30 minutes, which was then concentrated under reduced pressure and purified using silica gel chromatography (75% ethyl acetate in hexanes) to afford the final compound (0.39 g, 80%).

후처리

  1. customThe catalyst was removed by filtration with ethyl acetate through a bed of celite
  2. customThe compound was isolated
  3. temperaturethe mixture was warmed to r.t. for about 30 minutes
  4. concentrationwhich was then concentrated under reduced pressure
  5. custompurified

출처 및 근거

ORD 기록
ord-a5851dc30fcb49ae99b9f835e52812e4
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07186715B2

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