Hydrochloric Acid → {4-[(R)-2-((E)-(S)-3-hydroxy-oct-1-enyl)-5-oxo-pyrrolidin-1-yl]-butoxy}-acetic acid methyl ester
반응식
[CH3:1][O:2][C:3](=[O:25])[CH2:4][O:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C@@H:14](/[CH:15]=[CH:16]/[C:17](=[O:23])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:13][CH2:12][C:11]1=[O:24].O[C@@H](CCCCC)/C=C/[C@H]1CCC(=O)N1CCSCCCC(O)=O.B1(C)OC(C2C=CC=CC=2)(C2C=CC=CC=2)[C@@H]2N1CCC2.Cl>C1(C)C=CC=CC=1.CO>[CH3:1][O:2][C:3](=[O:25])[CH2:4][O:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:11](=[O:24])[CH2:12][CH2:13][C@@H:14]1/[CH:15]=[CH:16]/[C@@H:17]([OH:23])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]참가 물질
반응물 4
생성물 1
시약·촉매·용매 2
반응 조건
- 온도
- -26 °C
실험 절차
A solution of the {4-[(R)-2-Oxo-5-((E)-3-oxo-oct-1-enyl)-pyrrolidin-1-yl]-butoxy}-acetic acid methyl ester prepared as in Example 1 (250 mg, 0.71 mmol) in 10 mL of anhydrous toluene was added dropwise to a −26° C. solution of (R)-2-methyl-CBS-oxazaborolidine (Aldrich, 1 M in toluene, 0.35 mL) and borane-methyl sulfide complex (10 M, 0.07 mL). The reaction was stirred under nitrogen for 7 hours at −26° C. and then a solution of hydrochloric acid in methanol (2 M, 1-2 mL) was added. The solution was warmed to room temperature and the solvents were removed via reduced pressure. The crude residue was purified via silica gel chromatography yielding 11 mg of {4-[(R)-2-((E)-(S)-3-hydroxy-oct-1-enyl)-5-oxo-pyrrolidin-1-yl]-butoxy}-acetic acid methyl ester as an oil. This was taken directly on to the next step.
후처리
- temperatureThe solution was warmed to room temperature
- customthe solvents were removed via reduced pressure
- customThe crude residue was purified via silica gel chromatography
출처 및 근거
- ORD 기록
- ord-9867951d34004ba680da680bb5042dea
- 출처 데이터셋
- uspto-grants-2005_02
- 특허 번호
- US06849657B2
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