Aluminium lithium hydride → HCID 59497801, 화합물

HRID 1011511노트

반응식

HRID 1011511 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([S:14]([NH:17][C@H:18]2[CH2:22][CH2:21][CH2:20][C@H:19]2[C:23](OCC)=[O:24])(=[O:16])=[O:15])=[CH:10][CH:9]=1>O1CCCC1>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([S:14]([NH:17][C@@H:18]2[CH2:22][CH2:21][CH2:20][C@@H:19]2[CH2:23][OH:24])(=[O:15])=[O:16])=[CH:10][CH:9]=1

참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 90811846cis-Ethyl 2-(4-chlorophenylsulfonamido)cyclopentanecarboxylate

생성물 1

HCID 59497801HCID 59497801, 화합물수율 100.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A 1.0 M solution of lithium aluminum hydride in tetrahydrofuran (9.36 mL, 9.36 mmol) was added dropwise to a solution of cis-ethyl 2-(4-chlorophenylsulfonamido)cyclopentanecarboxylate (2.07 g, 6.24 mmol) in 40 mL anhydrous tetrahydrofuran under nitrogen at 0° C. The reaction was then stirred for 1 h at room temperature, then quenched by the slow addition of 100 mL ethyl acetate. The reaction was partitioned between 600 mL ethyl acetate and 300 mL saturated ammonium chloride. The organic layer was dried on sodium sulfate and concentrated to yield 4-chloro-N-(cis-2-(hydroxymethyl)cyclopentyl)benzenesulfonamide (1.81 g, 100%). 1H NMR (400 MHz, CDCl3) δ ppm 7.77-7.85 (2H, m), 7.45-7.50 (2H, m), 5.38 (1H, d, J=7.05 Hz), 3.61-3.78 (3H, m), 2.04-2.15 (1H, m), 1.27-1.80 (7H, m). LC/MS R.T.=2.46 min; [M+H]+=290.10.

후처리

  1. customquenched by the slow addition of 100 mL ethyl acetate
  2. customThe reaction was partitioned between 600 mL ethyl acetate and 300 mL saturated ammonium chloride
  3. customThe organic layer was dried on sodium sulfate
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-4840887b7fa34988ad7c16830b6ae509
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07977362B2

반응 노트

불러오는 중…