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Water → 1-((S)-7-Fluoro-2,3-dihydrobenzo[1,4]dioxin-2-ylmethyl)-3-methyl-3-[(S)-2-(tetrahydropyran-2-yloxy)ethoxymethyl]piperidine

HRID 2407316
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HRID 2407316 반응식
[CH3:1][C@:2]1([CH2:8][O:9][CH2:10][CH2:11][O:12][CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][O:14]2)[CH2:7][CH2:6][CH2:5][NH:4][CH2:3]1.[F:19][C:20]1[CH:21]=[CH:22][C:23]2[O:28][CH2:27][C@H:26]([CH2:29]OS(C)(=O)=O)[O:25][C:24]=2[CH:35]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[F:19][C:20]1[CH:21]=[CH:22][C:23]2[O:28][CH2:27][C@H:26]([CH2:29][N:4]3[CH2:5][CH2:6][CH2:7][C:2]([CH3:1])([CH2:8][O:9][CH2:10][CH2:11][O:12][C@H:13]4[CH2:18][CH2:17][CH2:16][CH2:15][O:14]4)[CH2:3]3)[O:25][C:24]=2[CH:35]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 66727215(S)-3-Methyl-3-[2-(tetrahydropyran-2-yloxy)ethoxymethyl]piperidineHCID 86644722methanesulfonic acid (R)-(7-fluoro-2,3-dihydrobenzo[1,4]dioxin-2-yl)methyl ester

생성물 1

HCID 667268271-((S)-7-Fluoro-2,3-dihydrobenzo[1,4]dioxin-2-ylmethyl)-3-methyl-3-[(S)-2-(tetrahydropyran-2-yloxy)ethoxymethyl]piperidine
수율 23.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

(S)-3-Methyl-3-[2-(tetrahydropyran-2-yloxy)ethoxymethyl]piperidine (100 mg, 0.39 mmol), methanesulfonic acid (R)-(7-fluoro-2,3-dihydrobenzo[1,4]dioxin-2-yl)methyl ester (102 mg, 0.39 mmol), K2CO3 (59 mg, 0.43 mmol) and KI (3 mg) were refluxed in dry DMF (3 ml) for 5 h. Water was added to the cooled mixture, followed by extraction with EtOAc (3×15 ml). The extracts were washed several times with water and finally with brine. After drying and filtering, the solvent was evaporated to give 143 mg of the crude product. This was chromatographed on silica (heptane/EtOAc, 70:30) to give 39 mg of the title compound as a colorless oil.

후처리

  1. extractionfollowed by extraction with EtOAc (3×15 ml)
  2. washThe extracts were washed several times with water
  3. customAfter drying
  4. filtrationfiltering
  5. customthe solvent was evaporated
  6. customto give 143 mg of the crude product
  7. customThis was chromatographed on silica (heptane/EtOAc, 70:30)

출처 및 근거

ORD 기록
ord-c085111c87de4baba1254213548db91a
출처 데이터셋
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08809536B2

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