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

HRID 73534

反応式

HRID 73534 の反応式
[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]

参加物

6

反応物 3

HCID 516892Sodium BicarbonateHCID 23665647Potassium tert-butoxideHCID 68922849HCID 68922849、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 73727Phosphonium, ethyltriphenyl-, bromide (1:1)触媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-e6f8476ce6314680b863fca27c4338a2
出典データセット
uspto-grants-2014_09
特許番号
US08829193B2

関連ノート

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