Water → 4-(2-Hydroxymethylfuran-3-yl)piperidine-1-carboxylic acid t-butyl ester

HRID 41631노트

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HRID 41631 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:18]=[CH:17][O:16][C:15]=2[C:19](OC)=[O:20])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:18]=[CH:17][O:16][C:15]=2[CH2:19][OH:20])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

6

반응물 4

HCID 962Water2회HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 584428164-(2-Methoxycarbonylfuran-3-yl)piperidine-1-carboxylic acid t-butyl ester

생성물 1

HCID 584428314-(2-Hydroxymethylfuran-3-yl)piperidine-1-carboxylic acid t-butyl ester수율 60.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

A solution of 4-(2-methoxycarbonylfuran-3-yl)piperidine-1-carboxylic acid t-butyl ester (2.0 g, 6.5 mmol, 1.0 eq.) in THF (60 mL) was added to a solution of LiAlH4 (490 mg, 13 mmol, 2.0 eq.) in THF (100 mL) at −30° C. The resulting solution was stirred for 1 hour and allowed to warm to 0° C., then stirred for 1 hour at 0° C. Water (0.5 mL) was added dropwise to quench the reaction. The mixture was allowed to warm to room temperature, and 15% NaOH (0.5 mL) and water (1.5 mL) was added. The solids were filtered and the filter cake was washed with EtOAc (50 mL). The filtrate was concentrated and the residue was applied onto a silica gel column and purified by chromatography with PE/EtOAc (10:1˜5:1), then by preparative HPLC to yield 4-(2-hydroxymethylfuran-3-yl)piperidine-1-carboxylic acid t-butyl ester (1.1 g) as a yellow oil.

후처리

  1. stirringstirred for 1 hour at 0° C
  2. customto quench
  3. customthe reaction
  4. temperatureto warm to room temperature
  5. filtrationThe solids were filtered
  6. washthe filter cake was washed with EtOAc (50 mL)
  7. concentrationThe filtrate was concentrated
  8. custompurified by chromatography with PE/EtOAc (10:1˜5:1)

출처 및 근거

ORD 기록
ord-6ae1e7844d9a4115a337282f9d9b5e41
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530663B2

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