تفاعل #690383

معادلة التفاعل

N-(3,4-dichlorophenyl)piperazine-1-carboxamide hydrochloride

N,N-diisopropylethylamine

NaBH(OAc)3

NaOH

Dess-Martin periodinane

tert-butyl (2R)-2-(hydroxymethyl)morpholine-4-carboxylate

sodium thiosulfate

→

title compound

المردود 24.1%

tert-Butyl (2S)-2-[(4-{[(3,4-dichlorophenyl)amino]carbonyl}piperazin-1-yl)methyl]-morpholine-4-carboxylate

المردود 24.1%

المذيبات

dichloromethane

DCM

ظروف التفاعل

المعالجة

1. 1
   أخرىthe DCM layer was removed
2. 2
   تجفيفthen dried (MgSO4)
3. 3
   ترشيحfiltered
4. 4
   أخرىevaporated
5. 5
   أخرىto form the crude aldehyde
6. 6
   workup.STIRRINGthe reaction was stirred under argon for 18 h
7. 7
   workup.STIRRINGby vigorous stirring
8. 8
   استخلاصthe dichloromethane layer was extracted
9. 9
   تجفيفThe organic layer was dried (MgSO4)
10. 10
    ترشيحfiltered
11. 11
    أخرىevaporated
12. 12
    أخرىPurification by chromatography (EtOAc neat)

الإجراء التجريبي

Dess-Martin periodinane (8.60 g) was added to tert-butyl (2R)-2-(hydroxymethyl)morpholine-4-carboxylate (4.00 g) in dry DCM at 0° C. The reaction was warmed to RT and stirred for a further 2 h. Aqueous sodium thiosulfate (10% w/v, 50 ml) was added and the DCM layer was removed then dried (MgSO4), filtered and evaporated to form the crude aldehyde. The residue was then dissolved in dry dichloromethane (100 ml) followed by addition of N-(3,4-dichlorophenyl)piperazine-1-carboxamide hydrochloride (5.72 g), N,N-diisopropylethylamine (3.17 mL) and NaBH(OAc)3 (9.76 g) and the reaction was stirred under argon for 18 h. 1M NaOH (50 mL) was added followed by vigorous stirring and the dichloromethane layer was extracted. The organic layer was dried (MgSO4), filtered and evaporated. Purification by chromatography (EtOAc neat) afforded the title compound (2.10 g) as a white foam LCMS M/z(+) 471, 473 (M+H+).

المصدر