(1R,2R)-2-(4-bromophenoxy)cyclopentan-1-ol → trans-2-(4-Bromophenoxy)cyclopentyl methanesulfonate

HRID 2360328노트

반응식

HRID 2360328 반응식
[CH3:1][S:2]([O:5][C@H:6]1[C@H:10]([O:11][C:12]2[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][CH:13]=2)[CH2:9]O[CH2:7]1)(=[O:4])=[O:3].Br[C:20]1C=CC(O[C@@H]2CCC[C@H]2O)=CC=1>>[CH3:1][S:2]([O:5][C@@H:6]1[CH2:7][CH2:20][CH2:9][C@H:10]1[O:11][C:12]1[CH:13]=[CH:14][C:15]([Br:18])=[CH:16][CH:17]=1)(=[O:3])=[O:4]

참가 물질

3

반응물 2

HCID 67195959(1R,2R)-2-(4-bromophenoxy)cyclopentan-1-olHCID 86653046trans-4-(4-Bromophenoxy)tetrahydrofuran-3-yl methanesulfonate

생성물 1

HCID 86653037trans-2-(4-Bromophenoxy)cyclopentyl methanesulfonate

실험 절차

The title compound of Step 2 was prepared according to the general procedure for the synthesis of trans-4-(4-bromophenoxy)tetrahydrofuran-3-yl methanesulfonate in Example 2, except that trans-2-(4-bromophenoxy)cyclopentanol was used in place of trans-4-(4-bromophenoxy)tetrahydrofuran-3-ol, and the reaction mixture was quenched by addition of saturated aqueous ammonium chloride solution. The organic layer was then washed with saturated aqueous ammonium chloride solution, washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and concentrated in vacuo to provide product as a brown oil. Yield: 3.86 g, 11.5 mmol, 98%. 1H NMR (400 MHz, CDCl3) δ 1.79-2.00 (m, 4H), 2.14-2.26 (m, 2H), 3.03 (s, 3H), 4.78 (m, 1H), 5.07 (m, 1H), 6.82 (d, J=9.0 Hz, 2H), 7.39 (d, J=9.1 Hz, 2H).

후처리

  1. customthe reaction mixture was quenched by addition of saturated aqueous ammonium chloride solution
  2. washThe organic layer was then washed with saturated aqueous ammonium chloride solution
  3. washwashed with saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto provide product as a brown oil

출처 및 근거

ORD 기록
ord-b1d602dc6e024012bc5af0e44f3086f9
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08686043B2

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