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Dichloromethane → 4-[3-(3-Benzyl-3,8-diazabicyclo[3.2.1]oct-8-yl)-2-hydroxypropoxy]benzonitrile

HRID 1743703
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인쇄 미리보기

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HRID 1743703 반응식
[CH2:1]([N:8]1[CH2:14][CH:13]2[NH:15][CH:10]([CH2:11][CH2:12]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:16]1[CH2:18][CH:17]1[CH2:19][O:20][C:21]1[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=1.C(Cl)Cl>CC(O)C.O>[CH2:1]([N:8]1[CH2:14][CH:13]2[N:15]([CH2:18][CH:17]([OH:16])[CH2:19][O:20][C:21]3[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=3)[CH:10]([CH2:11][CH2:12]2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 6344DichloromethaneHCID 27643014-(2-Oxiranylmethoxy)benzenecarbonitrileHCID 124305943-Benzyl-3,8-diazabicyclo[3.2.1]octane

생성물 1

HCID 222354394-[3-(3-Benzyl-3,8-diazabicyclo[3.2.1]oct-8-yl)-2-hydroxypropoxy]benzonitrile수율 89%

시약·촉매·용매 2

HCID 962Water용매
HCID 3776
Isopropanol
용매

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온도
60 °C

실험 절차

A mixture of 3-benzyl-3,8-diazabicyclo[3.2.1]octane (3.46 g, 17.1 mmol; from Preparation B, step (e) above) and 4-(2-oxiranylmethoxy)benzonitrile (3.00 g, 17.1 mmol; prepared as described in international patent application WO 99/31100) in 2-propanol (70 mL) and H2O (7 mL) was stirred at 60° C. for 22 h. The reaction mixture was concentrated in vacuo. The residue was dissolved in CH2Cl2 (200 mL) and washed with water (50 mL) and brine (50 mL). The organic layer was dried (NaSO4), filtered and concentrated in vacuo to give the crude product. Flash chromatography on silica gel eluting with CH2Cl2:CMA (8:1) gave 5.74 g (89%) of the sub-title compound as a yellow oil.

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved in CH2Cl2 (200 mL)
  3. washwashed with water (50 mL) and brine (50 mL)
  4. dry with materialThe organic layer was dried (NaSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give the crude product

출처 및 근거

ORD 기록
ord-22d5a7ff5b8b457da924a510e450c6b0
출처 데이터셋
uspto-grants-2006_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07012074B2

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