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

HRID 902336ノート

反応式

HRID 902336 の反応式
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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-eccfb132fbad46719b87ae525c02486c
出典データセット
uspto-grants-2008_04
特許番号
US07365095B2

反応ノート

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