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Tetrahydrofuran → HCID 12638305, compound

HRID 1903363
Notes
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Reaction equation

HRID 1903363 reaction equation
[O:1]=[C:2]1[NH:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH:3]1[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:18][CH:17]=1.C1COCC1.[H-].[Na+].Br[CH2:38][C:39]([O:41][CH3:42])=[O:40]>O>[C:11]([O:10][C:8]([N:4]1[CH2:5][CH2:6][N:7]([CH2:38][C:39]([O:41][CH3:42])=[O:40])[C:2](=[O:1])[CH:3]1[CH2:15][C:16]1[CH:17]=[CH:18][C:19]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:20][CH:21]=1)=[O:9])([CH3:13])([CH3:14])[CH3:12]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 12638302HCID 12638302, compound

Product 1

HCID 12638305HCID 12638305, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of t-boc-(4-benzyloxybenzyl) piperazinone 3a (2.66 g, 6.72 ×10-3 mole) and dry THF (20 ml) under argon at room temperature is added portionwise NaH (0.30 g, 7.4 ×10-3 mole, 59% oil dispersion). After stirring 1/2hour at room temperature a solution of methyl α-bromoacetate (0.62 ml, 7.4 ×10-3 mole) is added via syringe. After stirring overnight the reaction mixture is poured into water which is subsequently extracted with Et2O (3 times). The combined ethereal extracts are washed with saturated aqueous NaCl before being dried over Na2SO4. Filtration of the drying agent and evaporation of the filtrate affords a viscous oil which after column chromatography (silica gel, 10% EtOAc/CHCl3)gives a clear, colorless oil. After standing in the refrigerator this oil crystallizes. The resulting solid is triturated with hexane and collected by filtration affording 4a as colorless matted needles: 2.3 g (74%), m.p. 84°-87° C.

Workup

  1. additionis added via syringe
  2. extractionis subsequently extracted with Et2O (3 times)
  3. washThe combined ethereal extracts are washed with saturated aqueous NaCl
  4. dry with materialbefore being dried over Na2SO4
  5. filtrationFiltration of the drying agent and evaporation of the filtrate
  6. customaffords a viscous oil which after column chromatography (silica gel, 10% EtOAc/CHCl3)
  7. customgives a clear, colorless oil
  8. customcrystallizes
  9. customThe resulting solid is triturated with hexane
  10. filtrationcollected by filtration

Sources & evidence

ORD record
ord-28b67659267d4ac6ac38e8ef0c351e18
Source dataset
uspto-grants-1984_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04435571

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes