Water → Tert-butyl 3-((cyclopropylmethoxy)methyl)pyrrolidine-1-carboxylate

HRID 401801노트

반응식

HRID 401801 반응식
[OH:1][CH2:2][CH:3]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4]1.[H-].[Na+].Cl[CH2:18][CH:19]1[CH2:21][CH2:20]1.O>CN(C)C=O.C1COCC1>[CH:19]1([CH2:18][O:1][CH2:2][CH:3]2[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4]2)[CH2:21][CH2:20]1

참가 물질

7

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 80013(Chloromethyl)cyclopropaneHCID 5237175tert-Butyl 3-(hydroxymethyl)pyrrolidine-1-carboxylate

생성물 1

HCID 57732113Tert-butyl 3-((cyclopropylmethoxy)methyl)pyrrolidine-1-carboxylate수율 84.1%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of tert-butyl 3-(hydroxymethyl)pyrrolidine-1-carboxylate (Preparation 65, 46.6 g, 0.232 mol, 1 eq) in anhydrous dimethylformamide (250 mL) was added in portions with stirring and under an atmosphere of argon a dispersion in oil of sodium hydride (11.2 g, 0.28 mol, 1.2 eq) in oil. The mixture was stirred for 45 min and then (chloromethyl)cyclopropane (26 mL, 0.28 mol, 1.2 eq) in anhydrous THF (30 mL) was added. The mixture was stirred for 12 h and then treated with water (100 mL) and extracted with ether (3×200 mL). Ether fractions were washed with water (2×100 mL), dried over sodium sulfate and evaporated. The residue was subjected to chromatography (chloroform/ethylacetate 10:1) on silica to afford title compound (50 g, 0.195 mol, 84%).

후처리

  1. stirringThe mixture was stirred for 12 h
  2. extractionextracted with ether (3×200 mL)
  3. washEther fractions were washed with water (2×100 mL)
  4. dry with materialdried over sodium sulfate
  5. customevaporated

출처 및 근거

ORD 기록
ord-82323647352c41ca9b564354b465a54c
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08741934B2

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