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Sodium borohydride → tert-butyl 3-hydroxy-2-methylbutan-2-ylcarbamate

HRID 1850146
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HRID 1850146 반응식
[CH3:1][C:2]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])([C:4](=[O:6])[CH3:5])[CH3:3].[BH4-].[Na+]>CO>[OH:6][CH:4]([CH3:5])[C:2]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:1])[CH3:3]
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참가 물질

4

반응물 2

HCID 4311764Sodium borohydrideHCID 22973790tert-butyl N-(2-methyl-3-oxobutan-2-yl)carbamate

생성물 1

HCID 86730181tert-butyl 3-hydroxy-2-methylbutan-2-ylcarbamate수율 88.9%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of tert-butyl 2-methyl-3-oxobutan-2-ylcarbamate (2.36 g, 11.73 mmol) in MeOH (30 mL) at 0° C. was added portion wise NaBH4 (0.887 g, 23.45 mmol). Cold bath was removed and the reaction was stirred for 1 hour. HCl solution (1 M, 0.2 mL) was then added cautiously to quench the reaction. The reaction mixture was then concentrated and diluted with EtOAc (50 mL) and water (10 mL). The phases were separated and the aqueous layer was extracted with EtOAc (2×20 mL). The combined organics were then dried (Na2SO4) and concentrated under reduced pressure. The residue was purified via silica gel flash chromatography (10-50% EtOAc-Hexanes) to afford the desired product as a white solid (2.12 g). LCMS m/z 204.1 (M+H)+, Rt 0.69 min.

후처리

  1. customCold bath was removed
  2. additionHCl solution (1 M, 0.2 mL) was then added cautiously
  3. customto quench
  4. customthe reaction
  5. concentrationThe reaction mixture was then concentrated
  6. additiondiluted with EtOAc (50 mL) and water (10 mL)
  7. customThe phases were separated
  8. extractionthe aqueous layer was extracted with EtOAc (2×20 mL)
  9. dry with materialThe combined organics were then dried (Na2SO4)
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified via silica gel flash chromatography (10-50% EtOAc-Hexanes)

출처 및 근거

ORD 기록
ord-97bc390e53234788b002dc154cb3976c
출처 데이터셋
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08957068B2

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