tert-butyl (3S)-3-(hydroxymethyl)piperazine-1-carboxylate → (S)-tert-butyl 4-(2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)ethyl)-3-(hydroxymethyl)piperazine-1-carboxylate

HRID 1501936Notes

Reaction equation

HRID 1501936 reaction equation
[CH3:1][C:2]1[C:10]2[CH2:9][O:8][C:7](=[O:11])[C:6]=2[CH:5]=[CH:4][C:3]=1[CH:12]1[CH2:14][O:13]1.[C:15]([N:22]1[CH2:27][CH2:26][NH:25][C@H:24]([CH2:28][OH:29])[CH2:23]1)([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16]>C(O)C>[OH:29][CH2:28][C@H:24]1[N:25]([CH2:14][CH:12]([OH:13])[C:3]2[CH:4]=[CH:5][C:6]3[C:7](=[O:11])[O:8][CH2:9][C:10]=3[C:2]=2[CH3:1])[CH2:26][CH2:27][N:22]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:23]1

Participants

4

Reactant 2

HCID 24820294tert-butyl (3S)-3-(hydroxymethyl)piperazine-1-carboxylateHCID 552705554-Methyl-5-(oxiran-2-yl)-2-benzofuran-1(3H)-one

Product 1

HCID 71270662(S)-tert-butyl 4-(2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)ethyl)-3-(hydroxymethyl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
150 °C

Procedure

4-Methyl-5-oxiran-2-yl-2-benzofuran-1(3H)-one (3.00 g, 15.8 mmol) and (S)-4-N—BOC-2-hydroxymethylpiperazine (5.12 g. 23.7 mmol) were suspended in ethanol (10 mL) in a 20 mL microwave tube. The reaction mixture was degassed and heated in a microwave apparatus for 30 min at 150° C. The reaction mixture was evaporated to dryness, then chromatographed through a 330 g Redi-sep column and eluted with a solvent system of 1:1 EtOAc/hexane to 100% EtOAc to yield the title compound. LC-MS: M+1=407.

Workup

  1. customThe reaction mixture was degassed
  2. customThe reaction mixture was evaporated to dryness
  3. customchromatographed through a 330 g Redi-sep column
  4. washeluted with a solvent system of 1:1 EtOAc/hexane to 100% EtOAc

Sources & evidence

ORD record
ord-58ceea4e65dc4161beb5612a292e70a3
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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