1-Pentene, 5-bromo- → Methyl 4-(pent-4-en-1-yl)-1-(tert-butoxycarbonyl)piperidine-4-carboxylate

HRID 8744

반응식

HRID 8744 반응식
C[Si]([N-][Si](C)(C)C)(C)C.[K+].[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][CH:21]([C:24]([O:26][CH3:27])=[O:25])[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].Br[CH2:29][CH2:30][CH2:31][CH:32]=[CH2:33].C(=O)(O)[O-].[Na+]>O1CCCC1>[CH2:33]([C:21]1([C:24]([O:26][CH3:27])=[O:25])[CH2:22][CH2:23][N:18]([C:16]([O:15][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:17])[CH2:19][CH2:20]1)[CH2:32][CH2:31][CH:30]=[CH2:29]

참가 물질

6

반응물 4

HCID 707041-Pentene, 5-bromo-HCID 3928701-N-Boc-4-Piperidinecarboxylic acid methyl esterHCID 516892Sodium BicarbonateHCID 3251421Potassium bis(trimethylsilyl)amide

생성물 1

HCID 11232181Methyl 4-(pent-4-en-1-yl)-1-(tert-butoxycarbonyl)piperidine-4-carboxylate수율 99.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of potassium bis(trimethylsilyl)amide (30.7 g, 0.15 mol) in tetrahydrofuran (750 mL) at 0° C. was added a solution of methyl 1-(tert-butoxycarbonyl)piperidine-4-carboxylate (25 g, 0.10 mol) from Step A in tetrahydrofuran (250 mL) and the reaction mixture was stirred for 1 h. 5-Bromo-1-pentene (19.4 mL, 0.164 mol) was added and the reaction mixture was allowed to warm to room temperature for 1.5 h. The reaction mixture was then poured into saturated sodium bicarbonate solution and extracted three times with ethyl acetate. The organic layers were combined and washed with brine, dried over sodium sulfate, filtered, and concentrated to afford the title compound (30.9 g) which was used in the next step without further purification.

후처리

  1. extractionextracted three times with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-292d55b0aa854c219dbd269febe9a838
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091211B2

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