Water → tert-Butyl (4-hydroxy-2-methylbutan-2-yl)carbamate

HRID 1716542

반응식

HRID 1716542 반응식
[CH3:1][C:2]1([CH3:14])[N:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[C:4](=[O:13])[CH2:3]1.[BH4-].[Na+].O.[NH4+].[Cl-]>CO>[C:9]([O:8][C:6](=[O:7])[NH:5][C:2]([CH3:14])([CH3:1])[CH2:3][CH2:4][OH:13])([CH3:12])([CH3:10])[CH3:11]

참가 물질

6

반응물 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 10397866Tert-butyl 2,2-dimethyl-4-oxoazetidine-1-carboxylate

생성물 1

HCID 15473340tert-Butyl (4-hydroxy-2-methylbutan-2-yl)carbamate수율 80.5%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

4,4-Dimethyl-1-tert-butyloxycarbonyl-azetidine-2-one (32.5 g, synthesized according to Schoen et al., J. Med. Chem. 1994, 37 (7), 897) was dissolved in methanol (450 ml). The solution was cooled to 0° by means of an ice bath and treated with sodium borohydride (18.3 g, 6 portions over 45 minutes). The mixture was allowed to stir for 3 hours at 0°, warmed to room temperature and stirred for another 60 min. The reaction mixture was then poured into a mixture of ice, water and sat. NH4Cl solution and extracted with ether. The organic layer was separated, washed with brine, dried over Na2SO4 and evaporated. The residual oil was purified by flash chromatography (gradient of hexanes in ethyl acetate: 7/3 to 1/1). The fractions containing the product were combined, evaporated and dried in vacuo to leave a colorless oil (26.7 g).

후처리

  1. temperatureThe solution was cooled to 0° by means of an ice bath
  2. stirringstirred for another 60 min
  3. extractionextracted with ether
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. customevaporated
  8. customThe residual oil was purified by flash chromatography (gradient of hexanes in ethyl acetate: 7/3 to 1/1)
  9. additionThe fractions containing the product
  10. customevaporated
  11. customdried in vacuo

출처 및 근거

ORD 기록
ord-199fecc8b812428ebdba40f29dd28a55
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07803819B2

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