Trifluoroacetic acid → 3-(3-Chloro-5-fluorophenyl)pyrrolidin-3-ol

HRID 1931876노트

반응식

HRID 1931876 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([OH:21])[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10]2)[CH:5]=[C:6]([F:8])[CH:7]=1.FC(F)(F)C(O)=O.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([OH:21])[CH2:13][CH2:12][NH:11][CH2:10]2)[CH:5]=[C:6]([F:8])[CH:7]=1

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 67402932Tert-butyl 3-(3-chloro-5-fluorophenyl)-3-hydroxypyrrolidine-1-carboxylate

생성물 1

HCID 685156533-(3-Chloro-5-fluorophenyl)pyrrolidin-3-ol수율 64.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of tert-butyl 3-(3-chloro-5-fluorophenyl)-3-hydroxypyrrolidin-1-carboxylate (2.43 g, 7.7 mmol) in dichloromethane (80 mL), was added trifluoroacetic acid (5 mL). The mixture was stirred for 1.5 h after which the mixture was basified with aqueous sodium carbonate (10%, 50 mL) and evaporated. Ethyl acetate (100 mL) was added, the mixture was washed with brine and the organic phase was dried (MgSO4) and evaporated. Purification on a Biotage (solute SCX-3 SPE column (washed with methanol and eluted with methanol/triethylamine, 4:1), and by HPLC on Waters OBD 018, 5 μm (MeOH/33 mM NH3, 20:80 to 0:100), gave the title compound (1.07 g). MS m/z (rel. intensity, 70 eV) 215 (M+, bp), 157 (47), 129 (65), 109 (61), 95 (43).

후처리

  1. customevaporated
  2. additionEthyl acetate (100 mL) was added
  3. washthe mixture was washed with brine
  4. dry with materialthe organic phase was dried (MgSO4)
  5. customevaporated
  6. customPurification on a Biotage (
  7. washsolute SCX-3 SPE column (washed with methanol and eluted with methanol/triethylamine, 4:1)

출처 및 근거

ORD 기록
ord-eb06623c18db4faea1e0af3a75648618
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08188301B2

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