Triethylamine → 3-Fluoro-3-(1-methanesulfonyloxyethyl)pyrrolidine-1-carboxylic acid benzyl ester

HRID 10354노트

반응식

HRID 10354 반응식
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][C:13]([F:19])([CH:16]([OH:18])[CH3:17])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:27][S:28](Cl)(=[O:30])=[O:29]>ClCCl>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][C:13]([F:19])([CH:16]([O:18][S:28]([CH3:27])(=[O:30])=[O:29])[CH3:17])[CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 690767793-Fluoro-3-(1-hydroxyethyl)pyrrolidine-1-carboxylic acid benzyl ester

생성물 1

HCID 866071353-Fluoro-3-(1-methanesulfonyloxyethyl)pyrrolidine-1-carboxylic acid benzyl ester수율 95.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a −10° C. solution of 3-fluoro-3-(1-hydroxyethyl)pyrrolidine-1-carboxylic acid benzyl ester (Example A14, 0.267 g, 1.00 mmol), triethylamine (0.4 g, 4 mmol) and dichloromethane (10 mL) is added methanesulfonyl chloride (0.229 g, 2.00 mmol). The mixture is stirred at room temperature for 2 hours and concentrated in vacuo. The residue is partitioned between ethyl acetate and water. The organic layer is dried over Na2SO4 and concentrated to afford the title compound (0.330 g). 1H NMR (200 MHz, CDCl3): δ 7.36 (s, 5H), 5.14 (s, 2H), 4.99–4.81 (m, 1H), 3.76–3.37 (m, 4H), 3.06 (s, 3H), 2.25–1.96 (m, 2H), 1.52–1.47 (m, 3H).

후처리

  1. customTo a −10° C.
  2. concentrationconcentrated in vacuo
  3. customThe residue is partitioned between ethyl acetate and water
  4. dry with materialThe organic layer is dried over Na2SO4
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-f78574fb405d489d91af7e5ae9751dd2
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094780B1

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