Boron trifluoride → {7-chloro-6-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-3-methyl-1,2-benzoxazol-5-yl}methanol

HRID 245506ノート

反応式

HRID 245506 の反応式
[BH4-].[Na+].B(F)(F)F.B#B.[Cl:9][C:10]1[C:18]2[O:17][N:16]=[C:15]([CH3:19])[C:14]=2[CH:13]=[C:12]([C:20](O)=[O:21])[C:11]=1[N:23]1[CH2:28][C@H:27]([CH3:29])[O:26][C@H:25]([CH3:30])[CH2:24]1>COCCOCCOC.C1COCC1>[Cl:9][C:10]1[C:18]2[O:17][N:16]=[C:15]([CH3:19])[C:14]=2[CH:13]=[C:12]([CH2:20][OH:21])[C:11]=1[N:23]1[CH2:24][C@H:25]([CH3:30])[O:26][C@H:27]([CH3:29])[CH2:28]1

参加物

7

反応物 4

HCID 6356Boron trifluorideHCID 4311764Sodium borohydrideHCID 6328200DiboronHCID 673572387-chloro-6-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-3-methyl-1,2-benzoxazole-5-carboxylic acid2 回

生成物 1

HCID 67356497{7-chloro-6-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-3-methyl-1,2-benzoxazol-5-yl}methanol

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8150Diglyme溶媒

実験手順

To a stirred solution of NaBH4 (78 mg, 2.43 mmol) in diglyme (1 mL) was added BF3 (1.6 mL, 2.59 mmol), and the thus generated diborane gas was purged into solution of 7-chloro-6-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-3-methyl-1,2-benzoxazole-5-carboxylic acid (Intermediate 302, 250 mg, 0.8 mmol) in THF (1 mL). The mixture was stirred at room temperature for 30 minutes before being quenched with methanol (1 mL) and concentrated. The residue was purified by column chromatography to give product as solid. Yield: 130 mg (52%).

後処理

  1. custombefore being quenched with methanol (1 mL)
  2. concentrationconcentrated
  3. customThe residue was purified by column chromatography
  4. customto give product as solid

出典と根拠

ORDレコード
ord-c6dcf7c953e5453cb9a0719b9b717f07
出典データセット
uspto-grants-2014_02
特許番号
US08658641B2

反応ノート

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