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

HRID 571970노트

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HRID 571970 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6569Methyl Ethyl Ketone용매

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온도
60 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-66a48c60ac6c47f8a75cf4d4c77a06f6
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029368B2

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