Sodium borohydride → Tert-butyl 4-(2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)ethyl)-3-(2-hydroxyethyl)piperazine-1-carboxylate

HRID 1501971노트

반응식

HRID 1501971 반응식
[OH:1][CH2:2][CH2:3][CH:4]1[N:9]([CH2:10][C:11]([C:13]2[C:14]([CH3:23])=[C:15]3[C:19](=[CH:20][CH:21]=2)[C:18](=[O:22])[O:17][CH2:16]3)=[O:12])[CH2:8][CH2:7][N:6]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:5]1.[BH4-].[Na+]>CO>[OH:12][CH:11]([C:13]1[C:14]([CH3:23])=[C:15]2[C:19](=[CH:20][CH:21]=1)[C:18](=[O:22])[O:17][CH2:16]2)[CH2:10][N:9]1[CH2:8][CH2:7][N:6]([C:24]([O:26][C:27]([CH3:28])([CH3:29])[CH3:30])=[O:25])[CH2:5][CH:4]1[CH2:3][CH2:2][OH:1]

참가 물질

4

반응물 2

HCID 4311764Sodium borohydrideHCID 86727041Tert-butyl 3-(2-hydroxyethyl)-4-(2-(4-methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)-2-oxoethyl)piperazine-1-carboxylate

생성물 1

HCID 86727042Tert-butyl 4-(2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)ethyl)-3-(2-hydroxyethyl)piperazine-1-carboxylate

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

tert-Butyl 3-(2-hydroxyethyl)-4-(2-(4-methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)-2-oxoethyl)piperazine-1-carboxylate (6.16 g, 14.7 mmol) was dissolved in methanol (100 mL) at 0° C. and then NaBH4 (1.67 g, 44.2 mmol) was added. The reaction mixture was warmed up to RT. After ten minutes, TLC showed no SM left. The methanol was evaporated and the residue was taken up with brine and extracted with ethyl acetate twice. The combined organic layers were dried with MgSO4, filtered and concentrated. The crude product was chromatographed through an ISCO 330 g Redi-sep column and eluted with 5% MeOH/DCM to yield the title compound: LC-MS (IE, m/z): 421[M+1]+.

후처리

  1. waitAfter ten minutes
  2. waitleft
  3. customThe methanol was evaporated
  4. extractionextracted with ethyl acetate twice
  5. dry with materialThe combined organic layers were dried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was chromatographed through an ISCO 330 g Redi-sep column
  9. washeluted with 5% MeOH/DCM

출처 및 근거

ORD 기록
ord-39752a03b5934089a8fa03e2e10ab9e9
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09206199B2

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