反応 #156762

反応方程式

(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

収率 112.9%

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

収率 112.9%

溶媒

THF

反応条件

後処理

1. 1
   温度cooled to −78° C
2. 2
   温度to warm to −40° C.
3. 3
   workup.WAITfor 3 h
4. 4
   温度The reaction mixture was cooled to −60° C.
5. 5
   その他quenched with MeOH, water and TFA until a clear mixture
6. 6
   その他resulted
7. 7
   その他This was purified
8. 8
   workup.ADDITIONThe fractions containing product
9. 9
   濃縮were concentrated in vacuo
10. 10
    その他crystallized with ethyl ether
11. 11
    ろ過The solid was filtered
12. 12
    その他dried in vacuum

実験手順

(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.

出典