تفاعل #59644

معادلة التفاعل

sodium borohydride

acetate

[1-((S)-2-Benzyloxycarbonylamino-propyl)-7-bromo-1H-indazol-6-yloxy]-acetic acid ethyl ester

sodium borohydride

calcium chloride

→

solid

المردود 82.0%

{(S)-2-[7-Bromo-6-(2-hydroxy-ethoxy)-indazol-1-yl]-1-methyl-ethyl}-carbamic acid benzyl ester

المردود 82.0%

المذيبات

tetrahydrofuran

ethanol

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGThe suspension was stirred at ambient temperature for 1 h
2. 2
   أخرىThe volatiles were evaporated
3. 3
   workup.ADDITIONthe residue mixed with water
4. 4
   استخلاصextracted with ethyl acetate (3×50 mL)
5. 5
   تجفيفThe combined extracts were dried over magnesium sulfate
6. 6
   ترشيحfiltered
7. 7
   أخرىevaporated to dryness

الإجراء التجريبي

To a solution of the acetate from Step B (0.90 g, 1.84 mmol) in a mixture of tetrahydrofuran (20 mL) and ethanol (20 mL) was added sodium borohydride (70 mg, 1.84 mmol) and calcium chloride (0.21 g, 1.84 mmol) with stirring. The suspension was stirred at ambient temperature for 1 h and more sodium borohydride (70 mg, 1.84 mmol) was added. The reaction was monitored by TLC until no starting material remained. The volatiles were evaporated and the residue mixed with water and extracted with ethyl acetate (3×50 mL). The combined extracts were dried over magnesium sulfate, filtered and evaporated to dryness. Chromatography on silica eluting with a gradient of 20% to 50% EtOAc/hexane gave a solid (0.67 g, 82%): mp 97-99° C.; LCMS (+APCI) 448, 450 (M+H).

المصدر