Methanol → HCID 10341501, compound

HRID 358762Notes

Reaction equation

HRID 358762 reaction equation
CO.[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][N:13]([C:16](=[O:29])[C:17]2[CH:22]=[C:21]([O:23][CH3:24])[C:20]([O:25][CH3:26])=[C:19]([O:27][CH3:28])[CH:18]=2)[CH2:12][CH:11]1[C:30](OC)=[O:31])=[O:9])([CH3:6])([CH3:5])[CH3:4].[BH4-].[Na+].O1CCCC1>O>[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][N:13]([C:16](=[O:29])[C:17]2[CH:22]=[C:21]([O:23][CH3:24])[C:20]([O:25][CH3:26])=[C:19]([O:27][CH3:28])[CH:18]=2)[CH2:12][CH:11]1[CH2:30][OH:31])=[O:9])([CH3:5])([CH3:6])[CH3:4]

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 20066588HCID 20066588, compound

Product 1

HCID 10341501HCID 10341501, compoundYield 70.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methanol (6 ml) is added dropwise taking 30 minutes under reflux by heating, while stirring, to a mixture of methyl 1-tert-butoxycarbonyl-4-(3,4,5-trimethoxybenzoyl)piperazine-2-carboxylate (6.3 g), sodium borohydride (1.64 g) and tetrahydrofuran (80 ml). The reaction mixture is poured into water, followed by extraction with ethyl acetate. The organic layer is washed with water and dried, then the solvent is distilled off. Crystals obtained from the residue are recrystallized from ethyl acetate-ether to afford 1-tert-butoxycarbonyl-4-(3,4,5-trimethoxybenzoyl)piperazine-2-methanol (4.15 g) as colorless crystals, m.p. 119-120° C.

Workup

  1. temperatureunder reflux
  2. temperatureby heating
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer is washed with water
  5. customdried
  6. distillationthe solvent is distilled off
  7. customCrystals obtained from the residue
  8. customare recrystallized from ethyl acetate-ether

Sources & evidence

ORD record
ord-55053ce6b8c74b09bd27ad2547d66727
Source dataset
uspto-grants-1991_03
Patent number
US04997836

Reaction notes

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