Sodium hydride → Tert-butyl 4-{4-[[1-(methoxycarbonyl)-3-methylbutoxy](phenyl)methyl]benzoyl}piperazine-1-carboxylate

HRID 1180378Notes

Reaction equation

HRID 1180378 reaction equation
[OH:1][CH:2]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:3]1[CH:23]=[CH:22][C:6]([C:7]([N:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)=[O:8])=[CH:5][CH:4]=1.[H-].[Na+].Br[CH:33]([CH2:38][CH:39]([CH3:41])[CH3:40])[C:34]([O:36][CH3:37])=[O:35]>CN(C=O)C>[CH3:37][O:36][C:34]([CH:33]([O:1][CH:2]([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:3]1[CH:4]=[CH:5][C:6]([C:7]([N:9]2[CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:13][CH2:14]2)=[O:8])=[CH:22][CH:23]=1)[CH2:38][CH:39]([CH3:41])[CH3:40])=[O:35]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 12957039Methyl 2-bromo-4-methylpentanoateHCID 69470269Tert-butyl 4-{4-[hydroxy(phenyl)methyl]benzoyl}piperazine-1-carboxylate

Product 1

HCID 69473035Tert-butyl 4-{4-[[1-(methoxycarbonyl)-3-methylbutoxy](phenyl)methyl]benzoyl}piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl 4-{4-[hydroxy(phenyl)methyl]benzoyl}piperazine-1-carboxylate from step 3 (1.5 g, 3.8 mmol) in DMF (20 mL) at 0° C. was added sodium hydride (0.16 g, 4.0 mmol) portionwise. The mixture was aged 15 minutes under a nitrogen atmosphere and methyl 2-bromo-4-methylpentanoate (0.65 mL, 4.0 mmol) was added dropwise. The reaction was allowed to warm to room temperature and was aged for 3 hours. The mixture was then partitioned between ethyl acetate and brine and the organic layer was dried and evaporated. The crude product was chromatographed on silica gel using 40% ethyl acetate in hexanes to afford the title compound.

Workup

  1. waitwas aged for 3 hours
  2. customThe mixture was then partitioned between ethyl acetate and brine
  3. customthe organic layer was dried
  4. customevaporated
  5. customThe crude product was chromatographed on silica gel using 40% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-da1fcdbca44645f18fa98c05880649b8
Source dataset
uspto-grants-2007_10
Patent number
US07279478B2

Reaction notes

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