Hydrochloric Acid → (S)-4-benzyl 1-tert-butyl 2-(hydroxymethyl)piperazine-1,4-dicarboxylate

HRID 1006349노트

반응식

HRID 1006349 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[CH2:10][C@H:9]1[C:24](OCC)=[O:25])=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Li+].Cl.[Cl-].[Na+]>C(OCC)(=O)C.CO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[O:15])[CH2:10][C@H:9]1[CH2:24][OH:25])=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 4148881Lithium borohydrideHCID 59016652(S)-4-Benzyl 1-tert-butyl 2-ethyl piperazine-1,2,4-tricarboxylate

생성물 1

HCID 69745232(S)-4-benzyl 1-tert-butyl 2-(hydroxymethyl)piperazine-1,4-dicarboxylate수율 100.6%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8857Ethyl Acetate용매

실험 절차

Under nitrogen atmosphere, to a solution of (2S)-2-ethoxycarbonylpiperazine-1,4-dicarboxylic acid 4-benzyl ester 1-tert-butyl ester (9.35 g) was added portionwise lithium borohydride (1.82 g), and the reaction mixture was stirred for 90 minutes. After methanol (2.32 ml) was added dropwise to the solution under ice-cooling, the mixture was stirred at room temperature for 17 hours. 1N Hydrochloric acid (80 ml) was added dropwise under ice-cooling, and ethyl acetate (100 ml) and sodium chloride (6 g) was added to it. The organic layer was washed with brine, dried over magnesium sulfate, and evaporated under reduced pressure to give colorless oil. The oil was purified by column chromatography on silica gel (90 g) using a mixed solvent of hexane and ethyl acetate (3:2). The fractions containing the objective compound were collected and evaporated under reduced pressure to give (2S)-2-(hydroxymethyl)piperazine-1,4-dicarboxylic acid 4-benzyl ester 1-tert-butyl ester (8.40 g) as a colorless oil.

후처리

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 17 hours
  3. temperaturecooling
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under reduced pressure
  7. customto give colorless oil
  8. customThe oil was purified by column chromatography on silica gel (90 g)
  9. additionThe fractions containing the objective compound
  10. customwere collected
  11. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-061e190ebd084282b9261fe67d98dd1a
출처 데이터셋
uspto-grants-2004_09
특허 번호
US06787543B2

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