1,1'-((1R)-1-Methyl-1,2-ethanediyl)bis(diphenylphosphine) → (S)-1-[2-(tert-Butoxycarbonyl)-3-(2-methoxyethoxy)propyl]-1-cyclopentanecarboxylic acid

HRID 53457노트

반응식

HRID 53457 반응식
C1(N)CCCCC1.[C:8]([O:12][C:13](/[C:15](/[CH2:25][O:26][CH2:27][CH2:28][O:29][CH3:30])=[CH:16]/[C:17]1([C:22]([OH:24])=[O:23])[CH2:21][CH2:20][CH2:19][CH2:18]1)=[O:14])([CH3:11])([CH3:10])[CH3:9].C1(P(C2C=CC=CC=2)C[C@H](P(C2C=CC=CC=2)C2C=CC=CC=2)C)C=CC=CC=1>C1CC=CCCC=C1.C1CC=CCCC=C1.[Cl-].[Cl-].[Rh].[Rh]>[C:8]([O:12][C:13]([C@H:15]([CH2:25][O:26][CH2:27][CH2:28][O:29][CH3:30])[CH2:16][C:17]1([C:22]([OH:24])=[O:23])[CH2:21][CH2:20][CH2:19][CH2:18]1)=[O:14])([CH3:10])([CH3:9])[CH3:11]

참가 물질

4

반응물 2

HCID 27245391,1'-((1R)-1-Methyl-1,2-ethanediyl)bis(diphenylphosphine)HCID 67726576(E)-1-[2-(tert-butoxycarbonyl)-3-(2-methoxyethoxy)prop-1-enyl]-1-cyclopentanecarboxylic acid cyclohexylamine salt

생성물 1

HCID 11810308(S)-1-[2-(tert-Butoxycarbonyl)-3-(2-methoxyethoxy)propyl]-1-cyclopentanecarboxylic acid

시약·촉매·용매 1

HCID 6436379Rhodium, di-mu-chlorobis((1,2,5,6-eta)-1,5-cyclooctadiene)di-촉매

실험 절차

(E)-1-[2-(tert-Butoxycarbonyl)-3-(2-methoxyethoxy)prop-1-enyl]-1-cyclopentanecarboxylic acid cyclohexylamine salt (50 mg, 0.11 mmole), chloro(1,5-cyclooctadiene)rhodium(I)dimer (2.0 mg, 0.004 mmole) and (R)-(+)-1,2-bis(diphenylphosphino)propane (3.2 mg, 0.008 mmole) were charged to a glass vial and the top sealed with a rubber septum. The system was flushed with argon, methanol (0.5 mL) was added and the mixture hydrogenated in a steel bomb at 345 kPa (50 p.s.i.) and room temperature for 4 hours. The crude product was purified by chromatography on silica by eluting with diethyl ether/1% acetic acid to give, after combination and evaporation of appropriate fractions, the title compound as an oil, (22 mg, 61%) (ratio S:R 54.46), Rf =0.3 (ethyl acetate/hexane, 1:1+1% acetic acid).

후처리

  1. customthe top sealed with a rubber septum
  2. customThe system was flushed with argon, methanol (0.5 mL)
  3. additionwas added
  4. customThe crude product was purified by chromatography on silica
  5. washby eluting with diethyl ether/1% acetic acid
  6. customto give
  7. customafter combination and evaporation of appropriate fractions

출처 및 근거

ORD 기록
ord-b680dddbc2b3445da663b5ca49cf829e
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05618970

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