Water → (4R)-tert-butyl 2-(3-fluorophenyl)-4-hydroxypyrrolidine-1-carboxylate

HRID 513005노트

반응식

HRID 513005 반응식
[Si]([O:8][C@H:9]1[CH2:13][N:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:11]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=2)[CH2:10]1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-].O>C1COCC1>[F:27][C:23]1[CH:22]=[C:21]([CH:11]2[CH2:10][C@@H:9]([OH:8])[CH2:13][N:12]2[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:26]=[CH:25][CH:24]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 66684243(4R)-tert-butyl 4-(tert-butyldimethylsilyloxy)-2-(3-fluorophenyl)pyrrolidine-1-carboxylate

생성물 1

HCID 66684241(4R)-tert-butyl 2-(3-fluorophenyl)-4-hydroxypyrrolidine-1-carboxylate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of (4R)-tert-butyl 4-(tert-butyldimethylsilyloxy)-2-(3-fluorophenyl)pyrrolidine-1-carboxylate (I-3) (18.1 g, 38.2 mmol) in THF (76 mL) at room temperature was added TBAF (50 mL of a 1.0 M solution in THF, 49.7 mmol). The mixture was stirred at room temperature for 2 hours then poured into water. The mixture was extracted with EtOAc, washed with water and brine, dried over sodium sulfate, filtered and concentrated. The mixture was purified by column chromatography on silica gel with EtOAc/hexanes gradient as eluant to yield (4R)-tert-butyl 2-(3-fluorophenyl)-4-hydroxypyrrolidine-1-carboxylate (1-4). 1H NMR (400 MHz, CDCl3) δ 7.32-7.26 (m, 1 H), 7.07 (bd, J=7.6 Hz, 1 H), 7.01 (bd, J=7.5 Hz, 1 H), 6.92 (dt, J=8.4 Hz, 1 H), 4.83 (bs, 1 H), 4.50 (q, J=5.2 Hz, 1 H), 3.89 (bs, 1 H), 3.58 (ddd, J=1.2, 3.6, 12.0 Hz, 1 H), 2.62 (bs, 1 H), 2.0 (dt, J=4.4, 17.6 Hz, 1 H), 1.23 (s, 6 H). MS m/z 304.1 (M+23)+.

후처리

  1. extractionThe mixture was extracted with EtOAc
  2. washwashed with water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe mixture was purified by column chromatography on silica gel with EtOAc/hexanes gradient as eluant

출처 및 근거

ORD 기록
ord-3b11824cfc6b4a63813c880c248da912
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09102671B2

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