반응 #339591

반응 방정식

ethyl 2-tert-butoxycarbonylamino-4-[8-(2-methoxyethoxy)naphthalen-2-ylmethyl]-5-methylhexanoate

lithium borohydride

methanol

→

tert-butyl {1-hydroxymethyl-3-[8-(2-methoxyethoxy)naphthalen-2-ylmethyl]-4-methylpentyl}carbamate

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   농축the resulting mixture is concentrated by evaporation at 40° C
2. 2
   농축again concentrated by evaporation to dryness
3. 3
   추출extracted with dichloromethane (3×)—the combined organic phases
4. 4
   세척are washed with water
5. 5
   건조dried over sodium sulphate
6. 6
   농축concentrated by evaporation

실험 절차

A solution of 2.44 g of ethyl 2-tert-butoxycarbonylamino-4-[8-(2-methoxyethoxy)naphthalen-2-ylmethyl]-5-methylhexanoate in 35 ml of tetrahydrofuran is admixed at room temperature with 0.25 g of lithium borohydride in portions. After 23 hours, 35 ml of methanol are added dropwise and the resulting mixture is concentrated by evaporation at 40° C. The residue is once more admixed with 35 ml of methanol and again concentrated by evaporation to dryness. The residue is admixed with ice/1N HCl and extracted with dichloromethane (3×)—the combined organic phases are washed with water, dried over sodium sulphate and concentrated by evaporation. The title compound is identified on the basis of the Rf value from the residue by means of flash chromatography (SiO2 60F).

출처