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

HRID 2175792Notes

Reaction equation

HRID 2175792 reaction equation
[CH3:1][C:2]1[C:10]([C@H:11]2[CH2:13][O:12]2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][O:5][C:6]2=[O:14].[OH:15][CH2:16][C@H:17]1[NH:22][CH2:21][CH2:20][N:19]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:18]1>C(O)C>[OH:12][C@@H:11]([C:10]1[C:2]([CH3:1])=[C:3]2[C:7](=[CH:8][CH:9]=1)[C:6](=[O:14])[O:5][CH2:4]2)[CH2:13][N:22]1[CH2:21][CH2:20][N:19]([C:23]([O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[O:24])[CH2:18][C@H:17]1[CH2:16][OH:15]

Participants

4

Reactant 2

HCID 24820294tert-butyl (3S)-3-(hydroxymethyl)piperazine-1-carboxylateHCID 59568665(S)-4-methyl-5-(oxiran-2-yl)isobenzofuran-1(3H)-one

Product 1

HCID 86727037(S)-tert-butyl 4-((S)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)ethyl)-3-(hydroxymethyl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(S)-4-Methyl-5-(oxiran-2-yl)isobenzofuran-1(3H)-one (0.75 g, 3.95 mmol) and (S)-tert-butyl 3-(hydroxymethyl)piperazine-1-carboxylate (1.02 g, 4.73 mmol) in ethanol (12 mL) were heated in microwave at 150° C. for 1.5 h. The reaction solution was concentrated and the residue was purified by MPLC on a Biotage system using 40-100% ethyl acetate/hexane to give the title compound. LC/MS: (M+1)+: 407.15.

Workup

  1. concentrationThe reaction solution was concentrated
  2. customthe residue was purified by MPLC on a Biotage system

Sources & evidence

ORD record
ord-39a3a81a0fb14028938bcb7cfa8cf56a
Source dataset
uspto-grants-2015_06
Patent number
US09062070B2

Reaction notes

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