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 1501971Notes

Reaction equation

HRID 1501971 reaction equation
[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]

Participants

4

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-39752a03b5934089a8fa03e2e10ab9e9
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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