Dimethylformamide → Methyl 1-(4-ethynyl-3-fluorobenzyl)azetidine-3-carboxylate

HRID 2075184노트

반응식

HRID 2075184 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][C:16]=1[C:17]#[C:18][Si](C)(C)C)[CH2:5][N:6]1[CH2:9][CH:8]([C:10]([O:12][CH3:13])=[O:11])[CH2:7]1.[F-].[Cs+].CN(C=O)C>CO>[C:17]([C:16]1[CH:15]=[CH:14][C:4]([CH2:5][N:6]2[CH2:9][CH:8]([C:10]([O:12][CH3:13])=[O:11])[CH2:7]2)=[CH:3][C:2]=1[F:1])#[CH:18]

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 25953Cesium fluorideHCID 59651825Methyl 1-(3-fluoro-4-(2-(trimethylsilyl)ethynyl)benzyl)azetidine-3-carboxylate

생성물 1

HCID 25254788Methyl 1-(4-ethynyl-3-fluorobenzyl)azetidine-3-carboxylate

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Methyl 1-(3-fluoro-4-(2-(trimethylsilyl)ethynyl)benzyl)azetidine-3-carboxylate (20.9 g, 65 mmol), and cesium fluoride (11 g, 72 mmol), was added to DMF (50 mL). MeOH (100 mL) was added. After 2 h, MeOH was removed and the mixture was extracted with DCM and water. The organic layer is washed with brine and dried over magnesium sulfate. The solvent was removed and the material purified using Biotage (75 L, 7-100% EtOAc/hexanes) affording methyl 1-(4-ethynyl-3-fluorobenzyl)azetidine-3-carboxylate as light yellow oil. MS (ESI) m/z: Calculated: 247.1; Observed: 248.0 (M++1).

후처리

  1. customMeOH was removed
  2. extractionthe mixture was extracted with DCM and water
  3. washThe organic layer is washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed
  6. customthe material purified

출처 및 근거

ORD 기록
ord-fd7388fa60d9474c833e314ddbbab449
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07919519B2

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