Hydrochloric Acid → trans-3-Hydroxy-spiro[5.5]undecane-2-carboxylic acid methyl ester

HRID 2070539ノート

反応式

HRID 2070539 の反応式
[CH3:1][O:2][C:3]([CH:5]1[C:10](=[O:11])[CH2:9][CH2:8][C:7]2([CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[CH2:6]1)=[O:4].CO.[BH4-].[Na+].Cl>O1CCCC1>[CH3:1][O:2][C:3]([C@H:5]1[C@H:10]([OH:11])[CH2:9][CH2:8][C:7]2([CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[CH2:6]1)=[O:4].[CH3:1][O:2][C:3]([C@H:5]1[C@@H:10]([OH:11])[CH2:9][CH2:8][C:7]2([CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[CH2:6]1)=[O:4]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 4311764Sodium borohydrideHCID 577715873-Oxo-spiro[5.5]undecane-2-carboxylic acid methyl ester

生成物 2

HCID 68628437trans-3-Hydroxy-spiro[5.5]undecane-2-carboxylic acid methyl esterHCID 68629300cis-3-Hydroxy-spiro[5.5]undecane-2-carboxylic acid methyl ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 3-oxo-spiro[5.5]undecane-2-carboxylic acid methyl ester (29.6 g) obtained in Step 3 in a mixed solvent of methanol (200 mL)-tetrahydrofuran (50 mL), sodium borohydride (4.67 g) was added in three portions under ice-cooling, followed by stirring the reaction mixture under ice-cooling for 1 hour. Then, after addition of 1N aqueous hydrochloric acid solution to the reaction mixture, the resulting insolubles were filtered off. Methanol in the filtrate was evaporated off in vacuo, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:10 to 1:3) to give trans-3-hydroxy-spiro[5.5]undecane-2-carboxylic acid methyl ester (4.15 g) and cis-3-hydroxy-spiro[5.5]undecane-2-carboxylic acid methyl ester (4.9 g).

後処理

  1. temperaturecooling
  2. temperaturecooling for 1 hour
  3. filtrationthe resulting insolubles were filtered off
  4. customMethanol in the filtrate was evaporated off in vacuo
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe organic layer was washed with saturated brine
  7. customdried
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:10 to 1:3)

出典と根拠

ORDレコード
ord-17c4353e22564107bb6f1f8e31f714df
出典データセット
uspto-grants-2012_10
特許番号
US08299296B2

反応ノート

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