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Formic Acid → (R)-4-((S)-1-hydroxyethyl)-1-((S)-1-(4-methoxyphenyl)ethyl)pyrrolidin-2-one

HRID 715726
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HRID 715726 반응식
C1(C)C=CC(S(N[C@H](C2C=CC=CC=2)[C@@H](C2C=CC=CC=2)N)(=O)=O)=CC=1.[C:27]([C@H:30]1[CH2:34][N:33]([C@H:35]([C:37]2[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=2)[CH3:36])[C:32](=[O:45])[CH2:31]1)(=[O:29])[CH3:28].C(O)=O.Cl>C(#N)C.C[C]1[C](C)[C](C)[C](C)[C]1C.C[C]1[C](C)[C](C)[C](C)[C]1C.Cl[Rh]Cl.Cl[Rh]Cl.C(N(CC)CC)C>[OH:29][C@H:27]([C@H:30]1[CH2:34][N:33]([C@H:35]([C:37]2[CH:38]=[CH:39][C:40]([O:43][CH3:44])=[CH:41][CH:42]=2)[CH3:36])[C:32](=[O:45])[CH2:31]1)[CH3:28]
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참가 물질

8

반응물 4

HCID 284Formic AcidHCID 313Hydrochloric AcidHCID 2734565N-((1R,2R)-2-Amino-1,2-diphenylethyl)-4-methylbenzene-1-sulfonamideHCID 58071853(R)-4-Acetyl-1-((S)-1-(4-methoxyphenyl)ethyl)pyrrolidin-2-one

생성물 1

HCID 58071870(R)-4-((S)-1-hydroxyethyl)-1-((S)-1-(4-methoxyphenyl)ethyl)pyrrolidin-2-one수율 113.3%

시약·촉매·용매 3

HCID 16212157Bis[(pentamethylcyclopentadienyl)dichloro-rhodium]촉매HCID 6342Acetonitrile용매HCID 8471Triethylamine용매

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온도
-15 °C

실험 절차

2.4 g of Dichloro-(pentamethylcyclopentadienyl)-rhodium-(III)-dimer and 2.8 g (R,R)—N-(p-toluenesulfonyl)-1,2-diphenylethylendiamine [(R,R)-TsDPEN] is added to a solution of 50 g (R)-4-acetyl-1-[(S)-1-(4-methoxyphenyl)-ethyl]pyrrolidine-2-one in acetonitril at 25° C. The solution is cooled to −15° C. At this temperature a mixture of 22 mL formic acid and 135 mL triethylamine is added. The reaction mixture is stirred for 22 hours at −15° C. and then warmed up to 20° C. 230 mL of a 4 molar hydrochloric acid is added under cooling. The aqueous phase is extracted 3 times with ethyl acetate. The organic phase is washed with diluted and concentrated brine and treated with activated carbon. The organic phase is dried over sodium sulfate. The solvent is evaporated under reduced pressure to obtain 57.1 g of a beige solid with a diastereomeric purity of ˜97:3.

후처리

  1. additionis added
  2. temperaturewarmed up to 20° C
  3. temperatureunder cooling
  4. extractionThe aqueous phase is extracted 3 times with ethyl acetate
  5. washThe organic phase is washed
  6. additionwith diluted
  7. additionconcentrated brine and treated with activated carbon
  8. dry with materialThe organic phase is dried over sodium sulfate
  9. customThe solvent is evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-61b506fda00a4973bd9ed0302550fb6f
출처 데이터셋
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09187478B2

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