Hydrogen Peroxide → 1-tert-Butyl 3-methyl 4-(3-hydroxypropyl)piperidine-1,3-dicarboxylate

HRID 1644418노트

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HRID 1644418 반응식
[CH2:1]([CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH:5]1[C:17]([O:19][CH3:20])=[O:18])[CH:2]=[CH2:3].B1C2CCCC1CCC2.[OH-:30].[Na+].OO>O1CCCC1.C(OCC)(=O)C.O>[OH:30][CH2:3][CH2:2][CH2:1][CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:15])([CH3:16])[CH3:14])=[O:11])[CH2:6][CH:5]1[C:17]([O:19][CH3:20])=[O:18]

참가 물질

8

반응물 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 667752561-Tert-butyl 3-methyl 4-allylpiperidine-1,3-dicarboxylate

생성물 1

HCID 667751251-tert-Butyl 3-methyl 4-(3-hydroxypropyl)piperidine-1,3-dicarboxylate

시약·촉매·용매 3

HCID 962Water용매2회HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

실험 절차

A solution of 1-tert-butyl 3-methyl 4-allylpiperidine-1,3-dicarboxylate [WO2002/072572] (715 mg, 2.53 mmol) in tetrahydrofuran (5 mL) at 0° C. was treated with a solution of 9-BBN in tetrahydrofuran (0.5M, 10.2 mL, 5.1 mmol). After one hour the reaction mixture was allowed to warm to room temperature for 3 hours. The reaction mixture was cooled to 0° C. and treated with water (3 mL), NaOH (3N, 6 mL) and hydrogen peroxide (30% solution, 6 mL). The reaction was allowed to warm to room temperature and stir for one hour. The reaction was diluted with ethyl acetate and water. The layers were separated. The aqueous layer was extracted twice with ethyl acetate. The combined organic layers were dried over magnesium sulfate and concentrated at reduced. Chromatography on silica gel with methanol in dichloromethane (0-10%) gave the product as a colorless oil as a mixture of diastereomers (460 mg, 60%).

후처리

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. temperatureto warm to room temperature
  3. customThe layers were separated
  4. extractionThe aqueous layer was extracted twice with ethyl acetate
  5. dry with materialThe combined organic layers were dried over magnesium sulfate
  6. concentrationconcentrated at reduced

출처 및 근거

ORD 기록
ord-af4ed9dddcce412eb04461a55afd0e99
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08124602B2

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