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

HRID 577966Notes

Reaction equation

HRID 577966 reaction equation
[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

Participants

7

Reactant 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×

Product 1

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

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8150DiglymeSolvent

Procedure

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%).

Workup

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

Sources & evidence

ORD record
ord-cc78165e7f77485fbd508cf0458a154b
Source dataset
uspto-grants-2015_05
Patent number
US09040528B2

Reaction notes

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