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 2175798Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2175798
[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]

Komponenten

4

Edukt 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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

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]+.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-73a71ce3df3a43be8c42e0cb1c9a3965
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09062070B2

Notizen zur Reaktion

Wird geladen…