(S)-1-Boc-3-methylpiperazine → tert-butyl (3S)-4-[(2S)-2-hydroxy-3-(2-methylbenzothiazol-5-yloxy)propyl]-3-methylpiperazinecarboxylate

HRID 1245357Notes

Reaction equation

HRID 1245357 reaction equation
[CH3:1][C@@H:2]1[NH:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1.[CH3:15][C:16]1[S:17][C:18]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][C@H:27]3[CH2:29][O:28]3)=[CH:21][C:19]=2[N:20]=1>C(O)C>[OH:28][C@H:27]([CH2:26][O:25][C:22]1[CH:23]=[CH:24][C:18]2[S:17][C:16]([CH3:15])=[N:20][C:19]=2[CH:21]=1)[CH2:29][N:7]1[CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:13])([CH3:12])[CH3:14])=[O:9])[CH2:3][C@@H:2]1[CH3:1]

Participants

4

Reactant 2

HCID 7023035(S)-1-Boc-3-methylpiperazineHCID 210236065-(((R)-oxiran-2-yl)methoxy)-2-methylbenzo[d]thiazole

Product 1

HCID 86593854tert-butyl (3S)-4-[(2S)-2-hydroxy-3-(2-methylbenzothiazol-5-yloxy)propyl]-3-methylpiperazinecarboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of tert-butyl (3S)-3-methylpiperazinecarboxylate (3 g, 15 mmol) and 2-(2R)-methyl-5-(oxiran-2-ylmethoxy)benzothiazole, (3.3 g, 15 mmol), a compound of formula (5), was refluxed in ethanol for 24 hours. The solvent was removed under reduced pressure, and the residue was chromatographed on silica gel, eluting with methanol/dichloromethane 1/15, to yield tert-butyl (3S)-4-[(2S)-2-hydroxy-3-(2-methylbenzothiazol-5-yloxy)propyl]-3-methylpiperazinecarboxylate, a compound of formula (8).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was chromatographed on silica gel
  3. washeluting with methanol/dichloromethane 1/15

Sources & evidence

ORD record
ord-4a364f67d0a144d8831d41888a41f796
Source dataset
uspto-grants-2006_10
Patent number
US07125876B2

Reaction notes

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