Diisopropylethylamine → (S)-3-[4-(2-trimethylsilanyl-ethylsulfanyl)-phenyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 503925노트

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HRID 503925 반응식
[CH3:1][Si:2]([CH3:7])([CH3:6])[CH2:3][CH2:4][SH:5].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.CCN(C(C)C)C(C)C.[C:59]([O:63][C:64]([N:66]1[CH2:70][CH2:69][C@@H:68]([C:71]2[CH:76]=[CH:75][C:74](Br)=[CH:73][CH:72]=2)[CH2:67]1)=[O:65])([CH3:62])([CH3:61])[CH3:60].OS([O-])(=O)=O.[K+].[O-]S([O-])(=O)=O.[Na+].[Na+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:59]([O:63][C:64]([N:66]1[CH2:70][CH2:69][C@@H:68]([C:71]2[CH:76]=[CH:75][C:74]([S:5][CH2:4][CH2:3][Si:2]([CH3:7])([CH3:6])[CH3:1])=[CH:73][CH:72]=2)[CH2:67]1)=[O:65])([CH3:62])([CH3:60])[CH3:61]

참가 물질

8

반응물 5

HCID 81531DiisopropylethylamineHCID 2055212-(Trimethylsilyl)ethanethiolHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 59428435(S)-3-(4-bromo-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl esterHCID 86586342KHSO4 Na2SO4

생성물 1

HCID 59428461(S)-3-[4-(2-trimethylsilanyl-ethylsulfanyl)-phenyl]-pyrrolidine-1-carboxylic acid tert-butyl ester수율 100.3%

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 312751,4-Dioxane용매

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온도
97.5 °C

실험 절차

2-(Trimethylsilyl)ethane thiol (0.33 mL, 2.1 mmol), Pd2(dba)3 (183.9 mg), Xantphos (231.4 mg) and DIPEA (0.296 mL) were added to a solution of (S)-3-(4-bromo-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (528 mg, 1.618 mmol) in 1,4-dioxane (7 mL) under nitrogen atmosphere. The reaction mixture was heated at 95-100° C. for 20 hours. After cooling to room temperature, a solution of 10% KHSO4/Na2SO4 was added and the mixture was extracted with EtOAc. The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and evaporated under reduced pressure. The residue was purified via flash chromatography (hexane/EtOAc, 94/6) to give 616 mg (quantitative yield) of (S)-3-[4-(2-trimethylsilanyl-ethylsulfanyl)-phenyl]-pyrrolidine-1-carboxylic acid tert-butyl ester.

후처리

  1. temperatureAfter cooling to room temperature
  2. extractionthe mixture was extracted with EtOAc
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was purified via flash chromatography (hexane/EtOAc, 94/6)

출처 및 근거

ORD 기록
ord-bd20e92e6b154111965b251020c83993
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07776910B2

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