tert-butyl (3S)-3-(hydroxymethyl)piperazine-1-carboxylate → HCID 86727029, compound

HRID 1501965Notes

Reaction equation

HRID 1501965 reaction equation
[CH3:1][C@@H:2]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH:12]3[CH2:14][O:13]3)[CH:9]=2)[C:4](=[O:15])[O:3]1.[OH:16][CH2:17][C@H:18]1[NH:23][CH2:22][CH2:21][N:20]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:19]1>C(O)C>[OH:13][CH:12]([C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[C:4](=[O:15])[O:3][C@H:2]([CH3:1])[CH2:11]2)[CH2:14][N:23]1[CH2:22][CH2:21][N:20]([C:24]([O:26][C:27]([CH3:28])([CH3:29])[CH3:30])=[O:25])[CH2:19][C@H:18]1[CH2:17][OH:16]

Participants

4

Reactant 2

HCID 24820294tert-butyl (3S)-3-(hydroxymethyl)piperazine-1-carboxylateHCID 86693039(3R)-3-methyl-6-(oxiran-2-yl)-3,4-dihydro-1H-isochromen-1-one

Product 1

HCID 86727029HCID 86727029, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(3R)-3-methyl-6-(oxiran-2-yl)isochroman-1-one (0.750 g, 3.62 mmol) and (S)-tert-butyl 3-(hydroxymethyl)piperazine-1-carboxylate (0.953 g, 4.41 mmol) in ethanol (12 mL) was heated in microwave at 150° C. for 1.5 h. The reaction solution was concentrated and the residue was purified on Biotage using 40-100% ethyl acetate/hexane to give the title compound: LC/MS: (M+1)+: 421.15;

Workup

  1. concentrationThe reaction solution was concentrated
  2. customthe residue was purified on Biotage

Sources & evidence

ORD record
ord-49fce4ac9ae2498fad9753d46660927e
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

Loading…