Sodium Bicarbonate → (S)-benzyl 3-(tert-butoxycarbonylamino)-5-ethylidenepiperidine-1-carboxylate

HRID 73534

반응식

HRID 73534 반응식
[CH3:1][C:2](C)([O-])C.[K+].[C:7]([O:11][C:12]([NH:14][C@H:15]1[CH2:20][C:19](=O)[CH2:18][N:17]([C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:23])[CH2:16]1)=[O:13])([CH3:10])([CH3:9])[CH3:8].C(=O)(O)[O-].[Na+]>[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C.C1COCC1>[C:7]([O:11][C:12]([NH:14][C@H:15]1[CH2:20][C:19](=[CH:1][CH3:2])[CH2:18][N:17]([C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:23])[CH2:16]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]

참가 물질

6

반응물 3

HCID 516892Sodium BicarbonateHCID 23665647Potassium tert-butoxideHCID 68922849HCID 68922849, 화합물

생성물 1

HCID 68922866(S)-benzyl 3-(tert-butoxycarbonylamino)-5-ethylidenepiperidine-1-carboxylate

시약·촉매·용매 2

HCID 73727Phosphonium, ethyltriphenyl-, bromide (1:1)촉매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

To a suspension of ethyltriphenylphosphonium bromide (11 eq) in 14 mL of THF was added potassium tert-butoxide (10 eq) at room temperature. The reaction mixture was stirred at that temperature for 20 minutes. Then the reaction was cooled to 0° C., and (S)-benzyl 3-(tert-butoxycarbonylamino)-5-oxopiperidine-1-carboxylate (1 eq) in 7 mL of THF was added to the reaction mixture. The reaction was allowed to warm up room temperature. After being stirred for 40 minutes, the reaction mixture was poured into aq. sodium bicarbonate and extracted with ethyl acetate. The organic layer was separated and washed with brine, then dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The crude residue was purified by flash chromatography (EtOAc:hexanes=2:1) to yield (S)-benzyl 3-(tert-butoxycarbonylamino)-5-ethylidenepiperidine-1-carboxylate. LC/MS (m/z): 261.2 (MH+-100), Rt:1.12 min. HPLC: Rt:4.31 min.

후처리

  1. temperatureto warm up room temperature
  2. stirringAfter being stirred for 40 minutes
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude residue was purified by flash chromatography (EtOAc:hexanes=2:1)

출처 및 근거

ORD 기록
ord-e6f8476ce6314680b863fca27c4338a2
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829193B2

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