反応 #64608

反応方程式

triethylamine

triethylamine

6-benzyloxy-4-methoxymethyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid isopropyl ester

tert-butyl hypochlorite

→

6-benzyloxy-4-methoxymethyl-β-carboline-3-carboxylic acid isopropyl ester

収率 35.0%

溶媒

methylene chloride

methylene chloride

反応条件

後処理

1. 1
   workup.STIRRINGagitated for 2 hours at room temperature
2. 2
   濃縮Subsequently, the mixture is concentrated to one-half
3. 3
   抽出extracted once
4. 4
   workup.STIRRINGby shaking with dilute ammonia solution
5. 5
   その他The organic phase is dried
6. 6
   ろ過filtered
7. 7
   濃縮concentrated
8. 8
   その他The residue is chromatographed over silica gel with methylene chloride
9. 9
   その他Recrystallization from ethyl acetate

実験手順

A solution is prepared from 3.3 g (8.5 mmol) of 6-benzyloxy-4-methoxymethyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid isopropyl ester in 150 ml of methylene chloride, combined under argon with 3.9 ml of triethylamine, and cooled to -15° C. At this temperature, a solution of 3.2 ml (25.6 mmol) of tert-butyl hypochlorite in 50 ml of methylene chloride is added dropwise without delay to this solution. After the adding step is completed, the mixture is stirred for another 10 minutes, combined with 2.6 ml of triethylamine, and agitated for 2 hours at room temperature. Subsequently, the mixture is concentrated to one-half thereof and extracted once by shaking with dilute ammonia solution. The organic phase is dried, filtered, and concentrated. The residue is chromatographed over silica gel with methylene chloride:acetone=4:1 as the eluent. Recrystallization from ethyl acetate gives 1.1 g (35% yield) of 6-benzyloxy-4-methoxymethyl-β-carboline-3-carboxylic acid isopropyl ester, mp 150°-151° C.

出典