Sodium Azide → (R)-2-azidomethyl-8-(2-methoxyphenyl)-6-fluoro-chroman

HRID 902336노트

반응식

HRID 902336 반응식
CC1C=CC(S(O[CH2:12][C@H:13]2[CH:22]=[CH:21][C:20]3[C:15](=[C:16]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[O:30][CH3:31])[CH:17]=[C:18]([F:23])[CH:19]=3)[O:14]2)(=O)=O)=CC=1.[N-:32]=[N+:33]=[N-:34].[Na+]>CN(C=O)C>[N:32]([CH2:12][C@H:13]1[CH2:22][CH2:21][C:20]2[C:15](=[C:16]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[O:30][CH3:31])[CH:17]=[C:18]([F:23])[CH:19]=2)[O:14]1)=[N+:33]=[N-:34]

참가 물질

4

반응물 2

HCID 33557Sodium AzideHCID 86609125((R)-8-(2-methoxyphenyl)-6-fluoro-2H-chromen-2-yl)methyl 4-methylbenzenesulfonate

생성물 1

HCID 86609113(R)-2-azidomethyl-8-(2-methoxyphenyl)-6-fluoro-chroman수율 90.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution ((R)-8-(2-methoxyphenyl)-6-fluoro-2H-chromen-2-yl)methyl 4-methylbenzenesulfonate (300 mg, 0.67 mmol) and sodium azide (0.22 g, 3.4 mmol) in anhydrous DMF (20 mL) was heated to 90° C. under nitrogen for 20 hours. The cooled reaction mixture was quenched by the addition of water (30 mL) and the resulting suspension stirred vigorously for 10 minutes. The mixture was then partitioned between ethyl acetate (100 mL) and water (100 mL), the organic phase separated, washed with water (100 mL) and saturated brine (100 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. Chromatography with 0–30% ethyl acetate in hexanes afforded 190 mg (90%) of (2R)-2-azidomethyl-8-(2-methoxy-phenyl)-6-fluoro-chroman as a colorless oil.

후처리

  1. customThe cooled reaction mixture
  2. customwas quenched by the addition of water (30 mL)
  3. customThe mixture was then partitioned between ethyl acetate (100 mL) and water (100 mL)
  4. customthe organic phase separated
  5. washwashed with water (100 mL) and saturated brine (100 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-eccfb132fbad46719b87ae525c02486c
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07365095B2

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