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Ethanol → Tert-butyl 4-(1-carboxy-4-chlorobutan-1-yl)piperidine-1-carboxylate

HRID 546707
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HRID 546707 반응식
[OH-].[Na+].[Cl:3][CH2:4][CH2:5][CH2:6][CH:7]([CH:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1)[C:8]([O:10]CC)=[O:9].C(O)C.O>C1COCC1.C(OCC)C>[C:8]([CH:7]([CH:13]1[CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:17][CH2:18]1)[CH2:6][CH2:5][CH2:4][Cl:3])([OH:10])=[O:9]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 702EthanolHCID 962WaterHCID 14798Sodium HydroxideHCID 66839554Tert-butyl 4-(4-chloro-1-ethoxycarbonyl-butan-1-yl)piperidine-1-carboxylate

생성물 1

HCID 66839527Tert-butyl 4-(1-carboxy-4-chlorobutan-1-yl)piperidine-1-carboxylate수율 77.3%

시약·촉매·용매 2

HCID 3283
Diethyl Ether
용매
HCID 8028Tetrahydrofuran용매

실험 절차

A 5 N sodium hydroxide solution (3 ml) was added to a solution of tert-butyl 4-(4-chloro-1-ethoxycarbonyl-butan-1-yl)piperidine-1-carboxylate (1.76 g) in THF (5 ml)-ethanol (15 ml), and the reaction solution was stirred at room temperature for four days. Water and diethyl ether were added to the reaction solution, and the aqueous layer was separated. The aqueous layer was washed with diethyl ether again. Then, 5 N hydrochloric acid (3 ml) and ethyl acetate were added to the aqueous layer, and the organic layer was separated. The ethyl acetate extraction layer was washed with brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to obtain crude tert-butyl 4-(1-carboxy-4-chlorobutan-1-yl)piperidine-1-carboxylate (1.25 g).

후처리

  1. customthe aqueous layer was separated
  2. washThe aqueous layer was washed with diethyl ether again
  3. additionThen, 5 N hydrochloric acid (3 ml) and ethyl acetate were added to the aqueous layer
  4. customthe organic layer was separated
  5. extractionThe ethyl acetate extraction layer
  6. washwas washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-940b93d16f9940aaac6f0a19e00ee4b6
출처 데이터셋
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07935815B2

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