4-Toluenesulfonyl chloride → HCID 86729487, 화합물

HRID 712442노트

반응식

HRID 712442 반응식
[CH2:1]([N:8]1[CH2:12][CH:11]([CH2:13]O)[CH:10]([CH2:15][CH2:16][OH:17])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(CC)CC.S(Cl)(C1C=CC(C)=CC=1)(=O)=O>C1(C)C=CC=CC=1.CN(C1C=CN=CC=1)C>[CH2:1]([N:8]1[CH2:9][CH:10]2[CH2:15][CH2:16][O:17][CH2:13][CH:11]2[CH2:12]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 86729486HCID 86729486, 화합물

생성물 1

HCID 86729487HCID 86729487, 화합물수율 39%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 1140Toluene용매

실험 절차

To a solution of 2-(1-benzyl-4-(hydroxymethyl)pyrrolidin-3-yl) ethanol (0.50 g) in toluene (30 mL) was added Et3N (0.8 mL), TsCl (0.75 g) and DMAP (10 mg). The mixture was stirred for 12 h at room temperature under N2, washed with water, dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuo and the residue was used for the next step. To a solution of the above product in toluene (20 mL) was added Et3N (0.85 mL). The reaction mixture was heated to reflux for 4 h and cooled to room temperature. The reaction mixture was washed with water followed by brine. The mixture was dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was chromatographed with a silica gel column (eluting agent: 10:1 (v/v) CH2Cl2/CH3OH) to give the title compound (0.18 g, 13.61%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 218.3 (M+1).

후처리

  1. washwashed with water
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. additionTo a solution of the above product in toluene (20 mL) was added Et3N (0.85 mL)
  6. temperatureThe reaction mixture was heated
  7. temperatureto reflux for 4 h
  8. temperaturecooled to room temperature
  9. washThe reaction mixture was washed with water
  10. dry with materialThe mixture was dried over anhydrous Na2SO4
  11. concentrationconcentrated in vacuo
  12. customThe residue was chromatographed with a silica gel column (eluting agent: 10:1 (v/v) CH2Cl2/CH3OH)

출처 및 근거

ORD 기록
ord-931150dd0cee472e99461d9e150f145b
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181277B2

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