Reaktion #156762

Reaktionsgleichung

(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

Ausbeute 112.9%

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

Ausbeute 112.9%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled to −78° C
2. 2
   Temperaturto warm to −40° C.
3. 3
   workup.WAITfor 3 h
4. 4
   TemperaturThe reaction mixture was cooled to −60° C.
5. 5
   Sonstigequenched with MeOH, water and TFA until a clear mixture
6. 6
   Sonstigeresulted
7. 7
   SonstigeThis was purified
8. 8
   workup.ADDITIONThe fractions containing product
9. 9
   Einengenwere concentrated in vacuo
10. 10
    Sonstigecrystallized with ethyl ether
11. 11
    FiltrationThe solid was filtered
12. 12
    Sonstigedried in vacuum

Vorschrift

(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.

Quelle