Hydrochloric Acid → trans-1-Hydroxy-spiro[5.5]undecane-2-carboxylic acid methyl ester

HRID 2070582

반응식

HRID 2070582 반응식
[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][CH2:8][C:7]2([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[C:6]1=[O:16])=[O:4].[BH4-].[Na+].Cl>CO.[Cl-].[Na+].O>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:10][CH2:9][CH2:8][C:7]2([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]2)[C@H:6]1[OH:16])=[O:4]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 157014041-Oxo-spiro[5.5]undecane-2-carboxylic acid methyl ester

생성물 1

HCID 57771401trans-1-Hydroxy-spiro[5.5]undecane-2-carboxylic acid methyl ester수율 20.9%

시약·촉매·용매 2

HCID 887Methanol용매HCID 57417360Sodium chloride; water용매

실험 절차

To a solution of 1-oxo-spiro[5.5]undecane-2-carboxylic acid methyl ester (13.02 g) obtained in Step 2 in methanol (300 mL), sodium borohydride (2.2 g) was added in small portions under ice-cooling, followed by stirring the reaction mixture under ice-cooling for 30 minutes. Then, after addition of saturated brine, 2N aqueous hydrochloric acid solution was further added dropwise to the reaction mixture until the evolution of gases ceased, followed by extraction with ethyl acetate twice. 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)=1:8 to 1:5) to give trans-1-hydroxy-spiro[5.5]undecane-2-carboxylic acid methyl ester (2.74 g).

후처리

  1. temperaturecooling
  2. temperaturecooling for 30 minutes
  3. additionwas further added dropwise to the reaction mixture until the evolution of gases
  4. extractionfollowed by extraction with ethyl acetate twice
  5. washThe organic layer was washed with saturated brine
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:8 to 1:5)

출처 및 근거

ORD 기록
ord-6d02e91052154b89a5fcf10d0fc052e6
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08299296B2

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