Idramantone → Adamantane-1,4-diol

HRID 72121

반응식

HRID 72121 반응식
[OH:1][C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([C:5]3=[O:12])[CH2:3]1)[CH2:9]2.[BH4-].[Na+]>CO.Cl>[OH:1][C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH:5]3[OH:12])[CH2:3]1)[CH2:9]2

참가 물질

5

반응물 2

HCID 64184IdramantoneHCID 4311764Sodium borohydride

생성물 1

HCID 4252005Adamantane-1,4-diol

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 887Methanol용매

실험 절차

A stirred solution of 5-hydroxy-2-adamantanone (5.14 g, 30.9 mmol) in MeOH (100 mL) was cooled in an ice bath and three 1-g NaBH4 caplets (3 g, 78 mmol) were added. The mixture was allowed to warm to rt and stirred overnight. The mixture was diluted with 5% aq HCl (20 mL) and concentrated to dryness. The residue was taken up in EtOAc (200 mL), washed with water (25 mL) and brine (25 mL), and dried over Na2SO4. Removakl of the solvent left the title compound as a white solid (4.88 g, 94%) as a 1:1 mixture of cis and trans isomers.

후처리

  1. concentrationconcentrated to dryness
  2. washwashed with water (25 mL) and brine (25 mL)
  3. dry with materialdried over Na2SO4
  4. waitleft the title compound as a white solid (4.88 g, 94%)
  5. additionas a 1:1 mixture of cis and trans isomers

출처 및 근거

ORD 기록
ord-9754412822d547fbb4c6b2f37312bd09
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08828985B2

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