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

HRID 1795019Notes

Reaction equation

HRID 1795019 reaction equation
[O:1]1[CH2:3][C@@H:2]1[CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]2[S:13][C:12]([CH3:14])=[N:11][C:10]=2[CH:15]=1.[CH3:16][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)(CC)(C)C>[OH:1][C@@H:2]([CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]2[S:13][C:12]([CH3:14])=[N:11][C:10]=2[CH:15]=1)[CH2:3][N:22]1[CH2:21][CH2:20][N:19]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:18][C@@H:17]1[CH3:16]

Participants

4

Reactant 2

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

Product 1

HCID 21023610tert-butyl 4-[(2R)-2-hydroxy-3-(2-methylbenzothiazol-5-yloxy)propyl](3S)-3-methylpiperazinecarboxylateYield 85.7%

Reagents, catalysts & solvents 1

HCID 64052-Methyl-2-butanolSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 5-(((R)-oxiran-2-yl)methoxy)-2-methylbenzo[d]thiazole (3.24 g, 14.6 mmol) in tert-amyl alcohol (50 ml) was added (S)-tert-butyl 3-methylpiperazine-1-carboxylate (2.67 g, 13.3 mmol). The resulting mixture was stirred at 100° C. for 16 hours. It was then cooled, concentrated, and purified by chromatography (1:20 MeOH:CH2Cl2) to yield tert-butyl 4-[(2R)-2-hydroxy-3-(2-methylbenzothiazol-5-yloxy)propyl](3S)-3-methylpiperazinecarboxylate (4.8 g, 11.4 mmol).

Workup

  1. temperatureIt was then cooled
  2. concentrationconcentrated
  3. custompurified by chromatography (1:20 MeOH:CH2Cl2)

Sources & evidence

ORD record
ord-bc1a07b020324c7683456ffc04116604
Source dataset
uspto-grants-2006_04
Patent number
US07026321B2

Reaction notes

Loading…