Sodium Methoxide → (+)-(1R,2S,5R)-5-(hydroxymethyl)cyclopent-3-ene-1,2-diol

HRID 1504981ノート

反応式

HRID 1504981 の反応式
C([O:9][C@@H:10]1[C@@H:14]([CH2:15][OH:16])[CH:13]=[CH:12][C@@H:11]1[O:17]C(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C[O-].[Na+]>CO>[OH:16][CH2:15][C@@H:14]1[C@@H:10]([OH:9])[C@@H:11]([OH:17])[CH:12]=[CH:13]1

参加物

4

反応物 2

HCID 10942334Sodium MethoxideHCID 86693876HCID 86693876、化合物

生成物 1

HCID 86693877(+)-(1R,2S,5R)-5-(hydroxymethyl)cyclopent-3-ene-1,2-diol収率 71%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a stirred solution of (1R,2S,5R)-5-(hydroxymethyl)cyclopent-3-ene-1,2-diyl dibenzoate (7) (7.5 g, 22.1 mmol) in methanol at room temperature under N2 atmosphere was added drop wise sodium methoxide (25% by wt in methanol) (14.3 mL, 77.66 mmol) over a period of 20 minutes. The mixture was stirred at room temperature for 2 hr and quenched drop wise with 1N HCl solution to the pH neutral. The solvent was removed under reduced pressure and the obtained residue was purified by silica gel column chromatography (5% MeOH/DCM) to give triol 8 (2 g, 71%) as an oil; [α]24D+254.04° (c 1.0, MeOH); 1H NMR (500 MHz, CD3OD) δ 2.78 (d, J=5.0 Hz, 1H), 3.73 (dd, J=5.0, 11.0 Hz, 1H), 3.55 (dd, J=6.5, 10.5 Hz, 1H), 3.93 (t, 1H), 4.50 (t, 1H), 5.88-5.87 (m, 1H), 5.97 (d, J=6.0 Hz, 1H); 13C NMR (125 MHz, CD3OD) δ 53.7, 62.2, 73.2, 74.5, 132.0, 135.0; HR-MS Calcd. For (C6H10O3−H)+ 129.0630. found 129.0553.

後処理

  1. customquenched drop wise with 1N HCl solution to the pH neutral
  2. customThe solvent was removed under reduced pressure
  3. customthe obtained residue was purified by silica gel column chromatography (5% MeOH/DCM)

出典と根拠

ORDレコード
ord-25d29dec11014f99af56acf59321e7b0
出典データセット
uspto-grants-2015_12
特許番号
US09216960B2

反応ノート

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