Methanol → tert-butyl (1R*,4S*,6R*)-4-(hydroxymethyl)-3-azabicyclo[4.1.0]heptane-3-carboxylate

HRID 1426488

반응식

HRID 1426488 반응식
[N+](C1C=CC(C([O:12][CH2:13][C@@H:14]2[CH2:20][C@@H:19]3[C@@H:17]([CH2:18]3)[CH2:16][N:15]2[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=O)=CC=1)([O-])=O.O1CCCC1.CO.O.[OH-].[Li+]>[Cl-].[Na+].O.O>[OH:12][CH2:13][C@@H:14]1[CH2:20][C@@H:19]2[C@@H:17]([CH2:18]2)[CH2:16][N:15]1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22]

참가 물질

7

실험 절차

To a mixture of tert-butyl (1R*,4S*,6R*)-4-({[(4-nitrophenyl)carbonyl]oxy}methyl)-3-azabicyclo[4.1.0]heptane-3-carboxylate (8.2 g) produced above, tetrahydrofuran (70 mL), methanol (70 mL) and water (35 mL) was added lithium hydroxide monohydrate (2.7 g). The mixture was stirred at room temperature for 1 hr. The reaction mixture was diluted with brine, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate. Insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether) to give the title compound (3.5 g).

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous sodium sulfate
  3. filtrationInsoluble material was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether)

출처 및 근거

ORD 기록
ord-a71b1d1c5e57462695bcff5172dcbbda
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08933069B2

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