Sodium hydride → (S)-methyl 2-(4-benzyl-2-isopropylpiperazin-1-yl)benzoxazole-4-carboxylate

HRID 249865Notes

Reaction equation

HRID 249865 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][C@@H:10]([CH:14]([CH3:16])[CH3:15])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:20]1[O:21][C:22]2[C:23](=[C:25]([C:29]([O:31][CH3:32])=[O:30])[CH:26]=[CH:27][CH:28]=2)[N:24]=1>COCCOC>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:20]2[O:21][C:22]3[C:23](=[C:25]([C:29]([O:31][CH3:32])=[O:30])[CH:26]=[CH:27][CH:28]=3)[N:24]=2)[C@@H:10]([CH:14]([CH3:16])[CH3:15])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 17750438(3S)-1-Benzyl-3-(propan-2-yl)piperazineHCID 56924368Methyl 2-chlorobenzo[d]oxazole-4-carboxylate

Product 1

HCID 66874358(S)-methyl 2-(4-benzyl-2-isopropylpiperazin-1-yl)benzoxazole-4-carboxylateYield 54.3%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of (2S)-4-benzyl-2-isopropylpiperazine (363 mg, 1.66 mmol) in 1,2-dimethoxyethane (10 mL) at room temperature, was added NaH (80 mg, 1.66 mmol, 60% suspension in mineral oil) and the mixture was stirred for 1 h. Methyl 2-chlorobenzoxazole-4-carboxylate (351 mg, 1.66 mmol) was added to the reaction mixture and the reaction was stirred at room temperature for 17 h. The reaction mixture was quenched with CH3OH (10 mL), silica gel (15 mL) was added, and solvent removed under reduced pressure. The mixture was purified by column chromatography (silica gel, 0 to 100% EtOAc in hexanes) to afford (S)-methyl 2-(4-benzyl-2-isopropylpiperazin-1-yl)benzoxazole-4-carboxylate (355 mg, 54%) as a pale yellow oil. MS consistent.

Workup

  1. stirringthe reaction was stirred at room temperature for 17 h
  2. customThe reaction mixture was quenched with CH3OH (10 mL), silica gel (15 mL)
  3. additionwas added
  4. customsolvent removed under reduced pressure
  5. customThe mixture was purified by column chromatography (silica gel, 0 to 100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-6df55861ea0b4dbaae34bd7f07e7f631
Source dataset
uspto-grants-2011_01
Patent number
US07863271B2

Reaction notes

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