Lithium borohydride → benzyl tetrahydro-3-oxo-1H-oxazolo[3,4-a]pyrazine-7(3H)-carboxylate

HRID 618776ノート

反応式

HRID 618776 の反応式
C(O[C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[CH2:13][CH:12]1[C:27]([O:29]C)=O)=[O:10])C1C=CC=CC=1.[BH4-].[Li+]>O1CCCC1>[C:21]1([CH2:20][O:19][C:17]([N:14]2[CH2:15][CH2:16][N:11]3[C:9](=[O:10])[O:29][CH2:27][CH:12]3[CH2:13]2)=[O:18])[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

参加物

4

反応物 2

HCID 4148881Lithium borohydrideHCID 21847669(+/-)-Methyl N,N'-dibenzyloxycarbonylpiperazine-2-carboxylate

生成物 1

HCID 53668532benzyl tetrahydro-3-oxo-1H-oxazolo[3,4-a]pyrazine-7(3H)-carboxylate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a flask containing methyl N,N'-dibenzyloxycarbonylpiperazine-2-carboxylate (Step 2, 12.60 g, 30.60 mmol) and tetrahydrofuran (65 mL) at 0° C. under an inert atmosphere is added lithium borohydride (2 M in THF) (23.00 mL, 45.9 mmol). The solution is warmed to ambient temperature, stirred 19 hours, cooled to 0° C., and quenched with water (50 mL). The mixture is diluted with ethyl acetate (100 mL) and the pH is adjusted to 2 with 1N HCl. The layers are separated and the aqueous phase is extracted with ethyl acetate (50 mL). The organics are combined, washed with water (50 mL) and saline, dried over MgSO4, concentrated in vacuo, and chromatographed on silica gel (70-230 mesh, 500 g), eluting with hexane/ethyl acetate (50/50) then ethyl acetate (100). The appropriate fractions are combined (Rf =0.17, TLC, hexane/ethyl acetate, 50/50) and concentrated in vacuo to give the title compound, mp 85.5-86.5° C.

後処理

  1. temperaturecooled to 0° C.
  2. customquenched with water (50 mL)
  3. additionThe mixture is diluted with ethyl acetate (100 mL)
  4. customThe layers are separated
  5. extractionthe aqueous phase is extracted with ethyl acetate (50 mL)
  6. washwashed with water (50 mL) and saline
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customchromatographed on silica gel (70-230 mesh, 500 g)
  10. washeluting with hexane/ethyl acetate (50/50)
  11. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-32d3a2f2a6f84ee38a35a4b647a0489c
出典データセット
uspto-grants-1999_09
特許番号
US05955460

反応ノート

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