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

HRID 577966노트

반응식

HRID 577966 반응식
[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

참가 물질

7

반응물 4

HCID 6356Boron trifluorideHCID 4311764Sodium borohydrideHCID 6328200DiboronHCID 673572387-chloro-6-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-3-methyl-1,2-benzoxazole-5-carboxylic acid2회

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8150Diglyme용매

실험 절차

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%).

후처리

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

출처 및 근거

ORD 기록
ord-cc78165e7f77485fbd508cf0458a154b
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040528B2

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