Reaktion #332688

Reaktionsgleichung

NaBH4

BF3

diborane

7-chloro-6-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-3-methyl-1,2-benzoxazole-5-carboxylic acid

Intermediate 302

7-chloro-6-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-3-methyl-1,2-benzoxazole-5-carboxylic acid

→

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

Lösungsmittel

diglyme

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigebefore being quenched with methanol (1 mL)
2. 2
   Einengenconcentrated
3. 3
   SonstigeThe residue was purified by column chromatography
4. 4
   Sonstigeto give product as solid

Vorschrift

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%).

Quelle