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

HRID 53457ノート

反応式

HRID 53457 の反応式
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]

参加物

4

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

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

実験手順

(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).

後処理

  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

出典と根拠

ORDレコード
ord-b680dddbc2b3445da663b5ca49cf829e
出典データセット
uspto-grants-1997_04
特許番号
US05618970

反応ノート

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