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

HRID 53457

Reaktionsgleichung

Reaktionsgleichung von HRID 53457
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]

Komponenten

4

Edukt 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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

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

Versuchsvorschrift

(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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-b680dddbc2b3445da663b5ca49cf829e
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05618970

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