Sodium Carbonate → rac-(4aR*,8aR*)-tert-butyl 2-oxohexahydro-2H-pyrido[4,3-e][1,3]oxazine-7(3H)-carboxylate

HRID 571970ノート

反応式

HRID 571970 の反応式
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH:4]1[OH:16].C1N=CN([C:22](N2C=NC=C2)=[O:23])C=1.C([O-])([O-])=O.[Na+].[Na+]>CCC(C)=O>[O:23]=[C:22]1[NH:1][CH2:2][CH:3]2[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:10])[CH2:5][CH:4]2[O:16]1

参加物

5

反応物 3

HCID 10340Sodium CarbonateHCID 682631,1'-CarbonyldiimidazoleHCID 57306432Tert-butyl 4-(aminomethyl)-3-hydroxypiperidine-1-carboxylate

生成物 1

HCID 89602371rac-(4aR*,8aR*)-tert-butyl 2-oxohexahydro-2H-pyrido[4,3-e][1,3]oxazine-7(3H)-carboxylate収率 68.7%

試薬・触媒・溶媒 1

HCID 6569Methyl Ethyl Ketone溶媒

反応条件

温度
60 °C

実験手順

To a mixture of rac-(3R*,4R*)-tert-butyl 4-(aminomethyl)-3-hydroxypiperidine-1-carboxylate (3.39 g, 14.72 mmol; prepared according to Tetrahedron (2008), 64, 2456-2464) in MEK (40 mL) heated to 60° C. was added CDI (3.58 g, 22.08 mmol, 1.5 eq). The mixture was stirred for 3 h. Na2CO3 (5% aq., 4 mL) was added. The reaction proceeded at rt for 70 min. The two layers were decanted and the aq. layer was extracted with EA (10 mL). The combined org. layers were washed with brine (8 mL), dried over Na2SO4, filtered and concentrated to dryness. The residue was purified by CC (DCM to DCM/MeOH 9:1) to afford the title compound as a white solid (2.59 g).

後処理

  1. waitThe reaction proceeded at rt for 70 min
  2. customThe two layers were decanted
  3. extractionthe aq. layer was extracted with EA (10 mL)
  4. washlayers were washed with brine (8 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe residue was purified by CC (DCM to DCM/MeOH 9:1)

出典と根拠

ORDレコード
ord-66a48c60ac6c47f8a75cf4d4c77a06f6
出典データセット
uspto-grants-2015_05
特許番号
US09029368B2

反応ノート

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