Ammonium Chloride → Tert-butyl 2-hydroxy-7-azaspiro[3.5]nonane-7-carboxylate

HRID 47341노트

반응식

HRID 47341 반응식
[BH4-].[Na+].[O:3]=[C:4]1[CH2:7][C:6]2([CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]2)[CH2:5]1.[Cl-].[NH4+]>C(O)C>[OH:3][CH:4]1[CH2:7][C:6]2([CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]2)[CH2:5]1

참가 물질

5

반응물 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 11195798Tert-butyl 2-oxo-7-azaspiro[3.5]nonane-7-carboxylate

생성물 1

HCID 9834677Tert-butyl 2-hydroxy-7-azaspiro[3.5]nonane-7-carboxylate수율 93.3%

시약·촉매·용매 1

HCID 702Ethanol용매2회

실험 절차

300 ml ethanol was ice-cooled, and 6.13 g of sodium borohydride was dissolved therein. 100 ml solution of 38.9 g of tert-butyl 2-oxo-7-azaspiro[3.5]nonane-7-carboxylate in ethanol was added dropwise thereinto over 25 min. The reaction solution was treated with saturated aqueous ammonium chloride and evaporated. The resulting residue was partitioned into ethyl acetate and water, and the ethyl acetate layer was washed with brine and dried over magnesium sulfate. After filtration, the solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give 36.6 g of tert-butyl 2-hydroxy-7-azaspiro[3.5]nonane-7-carboxylate.

후처리

  1. temperaturecooled
  2. customevaporated
  3. customThe resulting residue was partitioned into ethyl acetate and water
  4. washthe ethyl acetate layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationAfter filtration
  7. customthe solvent was evaporated
  8. customthe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-8cec20f9ce3748df98c93be41ac17ce9
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06699870B2

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