반응 #156762

반응 방정식

(S)-methyl 6-oxo-5,6,6a,7,8,9-hexahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazine-3-carboxylate

sodium hydride

LiAlH4

→

title compound

수율 112.9%

(S)-3-(hydroxymethyl)-6a,7,8,9-tetrahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazin-6(5H)-one

수율 112.9%

용매

THF

반응 조건

후처리

1. 1
   온도cooled to −78° C
2. 2
   온도to warm to −40° C.
3. 3
   workup.WAITfor 3 h
4. 4
   온도The reaction mixture was cooled to −60° C.
5. 5
   기타quenched with MeOH, water and TFA until a clear mixture
6. 6
   기타resulted
7. 7
   기타This was purified
8. 8
   workup.ADDITIONThe fractions containing product
9. 9
   농축were concentrated in vacuo
10. 10
    기타crystallized with ethyl ether
11. 11
    여과The solid was filtered
12. 12
    기타dried in vacuum

실험 절차

(S)-methyl 6-oxo-5,6,6a,7,8,9-hexahydropyrido[3,2-e]pyrrolo[1,2-a]pyrazine-3-carboxylate (3.00 g, 10.5 mmol) was suspended in THF and sodium hydride (60% suspension in mineral oil, 0.712 g, 17.8 mmol) was added under nitrogen atmosphere. The reaction mixture was stirred at room temperature for 1 h and cooled to −78° C. LiAlH4 (2M in THF, 12.5 mL, 25 mmol) was added dropwise over 5 min and the reaction mixture was allowed to warm to −40° C. and kept at −40-(−20)° C. for 3 h. The reaction mixture was cooled to −60° C. and quenched with MeOH, water and TFA until a clear mixture resulted. This was purified using HPLC (1-30% acetnitrile in water, TFA buffered). The fractions containing product were concentrated in vacuo and crystallized with ethyl ether. The solid was filtered and dried in vacuum to afford the title compound as a grey solid (2.60 g, 74%, TFA salt). [M+H] calc'd for C11H13N3O2, 220; found, 220.

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