Reaktion #40468

Reaktionsgleichung

4-benzyl-6-iodomethyl-6-methyl-morpholine-3-carboxylic acid benzyl ester

Intermediate 17

4-benzyl-6-iodomethyl-6-methyl-morpholine-3-carboxylic acid benzyl ester

tributyltin hydride

AIBN

→

4-benzyl-6,6-dimethyl-morpholine-3-carboxylic acid benzyl ester

Ausbeute 85.0%

Lösungsmittel

toluene

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto cool down
2. 2
   Einengenwas concentrated to dryness
3. 3
   SonstigeThe residue was partitioned into 15% 1M HCl in acetonitrile and hexane
4. 4
   ExtraktionThe separated hexane phase was extracted two times with the acetonitrile solution
5. 5
   WaschenThe combined acetonitrile solutions were washed with hexane two times
6. 6
   Einengenconcentrated
7. 7
   SonstigeThe residue was partitioned into ether and 1M K2CO3
8. 8
   WaschenThe separated ether phase was washed successively with 0.4M Na2S2O3 and brine
9. 9
   Trocknendried over MgSO4
10. 10
    Einengenconcentrated
11. 11
    SonstigeThe residue was purified on silica (7.5% EtOAc/hexane)

Vorschrift

To a solution of 4-benzyl-6-iodomethyl-6-methyl-morpholine-3-carboxylic acid benzyl ester (Intermediate 17, 1.23 g) and tributyltin hydride (1.8 ml, 2.5 eq.) in 11 ml of toluene under gentle reflux was added over 1.5 hr a solution of AIBN in toluene (25 mg/1 ml). The mixture was allowed to cool down and was concentrated to dryness. The residue was partitioned into 15% 1M HCl in acetonitrile and hexane. The separated hexane phase was extracted two times with the acetonitrile solution. The combined acetonitrile solutions were washed with hexane two times and concentrated. The residue was partitioned into ether and 1M K2CO3. The separated ether phase was washed successively with 0.4M Na2S2O3 and brine, dried over MgSO4 and concentrated. The residue was purified on silica (7.5% EtOAc/hexane) to give 760 mg (oil, 85% yield) of compound 4-benzyl-6,6-dimethyl-morpholine-3-carboxylic acid benzyl ester.

Quelle