Water → (S)-OCTAHYDRO-PYRIDO[1,2-A]PYRAZINE

HRID 500443Notes

Reaction equation

HRID 500443 reaction equation
O=[C:2]1[NH:7][CH2:6][C:5](=O)[N:4]2[CH2:9][CH2:10][CH2:11][CH2:12][C@@H:3]12.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH2:2]1[NH:7][CH2:6][CH2:5][N:4]2[CH2:9][CH2:10][CH2:11][CH2:12][C@@H:3]12

Participants

6

Conditions

Temperature
0 °C

Procedure

(S)-Octahydro-1,4-dioxo-2H-pyrido[1,2-a]pyrazine (0.5 g, 2.98 mmol) was added portionwise to a stirred solution of lithium aluminium hydride (1M in tetrahydrofuran; 11.9 ml, 11.9 mmol). The resulting mixture was heated under reflux for 0.5 h. The solution was then cooled to 0° C. and treated dropwise with water (1.35 ml), 1 M sodium hydroxide solution (0.45 ml), then water (1.35 ml). Tetrahydrofuran (10 ml) was added and the solution stirred for 0.5 h, before filtration. The filter cake was washed with tetrahydrofuran (2×5 ml) and the combined filtrate and washings concentrated to yield (S)-octahydro-2H-pyrido[1,2-a]pyrazine as a yellow oil (0.29 g, 2.07 mmol).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 0.5 h
  3. washThe filter cake was washed with tetrahydrofuran (2×5 ml)
  4. concentrationthe combined filtrate and washings concentrated

Sources & evidence

ORD record
ord-5ad6a31487d34da289996b4d699885d7
Source dataset
uspto-grants-2010_08
Patent number
US07772227B2

Reaction notes

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