Oxygen → (2-Hydroxy-3-oxo-cyclopent-1-enyl)-acetic acid

HRID 1430721

反応式

HRID 1430721 の反応式
[CH:1]1([CH2:6][C:7]([OH:9])=[O:8])[CH2:5][CH2:4][CH:3]=[CH:2]1.C[N+]1([O-])CC[O:14]CC1.O=O.[Li+].[OH-:21]>O.CC(O)(C)C.OC1C(O)CCC=1CC(O)=O.[Pt].CC#N.O.O=[Os](=O)(=O)=O>[OH:21][C:2]1[C:3](=[O:14])[CH2:4][CH2:5][C:1]=1[CH2:6][C:7]([OH:9])=[O:8]

参加物

10

反応物 4

HCID 977OxygenHCID 3939Lithium HydroxideHCID 82029Methyl morpholine oxideHCID 962162-Cyclopentene-1-acetic acid3 回

生成物 1

HCID 67291543(2-Hydroxy-3-oxo-cyclopent-1-enyl)-acetic acid収率 28%

試薬・触媒・溶媒 5

HCID 23939Platinum触媒HCID 30318Osmium Tetroxide触媒HCID 18373917Acetonitrile--water (1/1)溶媒HCID 714019492-Methylpropan-2-ol--water (1/1)溶媒HCID 131732373(2,3-Dihydroxycyclopentenyl)-acetic acid溶媒

実験手順

The only publication describing the preparation procedure of (2-hydroxy-3-oxo-cyclopent-1-enyl)-acetic acid esters, particularly the corresponding tAm ester is described by Reile et al. (Reile I., Paju, A.; Eek, M.; Pehk, T.; Lopp, M. Aerobic Oxidation of Cyclopentane-1,2-diols to Cyclopentane-1,2-diones on Pt/C Catalyst. Synlett, 2008 (3), 347-350). According to that procedure 2-cyclopentene-1-acetic acid is transformed to 2-cyclopentene-1-acetic acid tAm ester by transesterification according to a known procedure (Frei, U., Kirchmayr, R. EP 0278914). The resulted 2-cyclopentene-1-acetic acid tAm ester is dihydroxylated by using fiber bound OsO4 (0.1 mol %) and NMO (1.3 equiv) in H2O-tBuOH 1:3 mixture at 60° C., resulting in (2,3-dihydroxycyclopentenyl)-acetic acid tAm ester. This compound is oxidized with air oxygen in the presence of 5 mol % Pt/C catalyst in MeCN—H2O 1:1 mixture, in the presence of 1 equivalent of LiOH. The target compound (2-hydroxy-3-oxo-cyclopent-1-enyl)-acetic acid tAm ester was obtained in 28% yield after separation and purification.

後処理

  1. customat 60° C.

出典と根拠

ORDレコード
ord-49cfe180e1964bb7a88bee812b09555b
出典データセット
uspto-grants-2015_01
特許番号
US08940920B2

関連ノート

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