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Acetic Acid → Tert-butyl 4-oxo-3-(3-(tetrahydrofuran-2-yl)propanoyl)piperidine-1-carboxylate

HRID 1930724
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인쇄 미리보기

반응식

HRID 1930724 반응식
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[O:11]=[C:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1.N1([C:30](=[O:38])[CH2:31][CH2:32][CH:33]2[CH2:37][CH2:36][CH2:35][O:34]2)C=CN=C1.C(O)(=O)C>C1(C)C=CC=CC=1.O>[O:11]=[C:12]1[CH2:13][CH2:14][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:16][CH:17]1[C:30](=[O:38])[CH2:31][CH2:32][CH:33]1[CH2:37][CH2:36][CH2:35][O:34]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 2733832Lithium hexamethyldisilazaneHCID 593337451-(1H-imidazol-1-yl)-3-(tetrahydrofuran-2-yl)propan-1-one

생성물 1

HCID 59333690Tert-butyl 4-oxo-3-(3-(tetrahydrofuran-2-yl)propanoyl)piperidine-1-carboxylate수율 38.9%

시약·촉매·용매 2

HCID 962
Water
용매
HCID 1140Toluene용매2회

실험 절차

Lithium bis(trimethylsilyl)amide (2.231 ml, 11.88 mmol) was added to a stirred solution of tert-butyl 4-oxopiperidine-1-carboxylate (1.127 g, 5.66 mmol) in toluene (3 mL) at 0° C. and the resulting mixture was stirred for 2 minutes. 1-(1H-Imidazol-1-yl)-3-(tetrahydrofuran-2-yl)propan-1-one (1.099 g, 5.66 mmol) in toluene (1 mL) was added and the reaction mixture was stirred for 5 minutes before it was quenched with acetic acid (0.972 ml, 16.97 mmol) in water (4 mL). The organic layer was separated and purified by silica flash chromatography using a gradient of ethyl acetate in heptane (0 to 40%) giving tert-butyl 4-oxo-3-(3-(tetrahydrofuran-2-yl)propanoyl)piperidine-1-carboxylate (0.717 g, 38.9%) as the product.

후처리

  1. stirringthe reaction mixture was stirred for 5 minutes before it
  2. customThe organic layer was separated
  3. custompurified by silica flash chromatography

출처 및 근거

ORD 기록
ord-566de2f90d7f433e9eeefc5257f1e99b
출처 데이터셋
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08188101B2

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