Methanol → tert-butyl N-{[3-(hydroxymethyl)-4-nitrophenyl]methyl}carbamate

HRID 862599Notes

Reaction equation

HRID 862599 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([N+:20]([O-:22])=[O:21])=[C:14]([CH:19]=1)[C:15](OC)=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].CO.S([O-])(O)(=O)=O.[K+]>C1COCC1>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([N+:20]([O-:22])=[O:21])=[C:14]([CH:19]=1)[CH2:15][OH:16])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 887MethanolHCID 516920Potassium bisulfateHCID 4311764Sodium borohydrideHCID 19698365Methyl 5-tert-butoxycarbonylaminomethyl-2-nitrobenzoate

Product 1

HCID 19698378tert-butyl N-{[3-(hydroxymethyl)-4-nitrophenyl]methyl}carbamateYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 5-tert-butoxycarbonylaminomethyl-2-nitrobenzoate (2.0 g, 6.45 mmol) and sodium borohydride (740 mg, 19.56 mmol) in THF (11 mL) was added dropwise methanol (1.5 mL) over 1.5 h under reflux. After the addition was completed, the excess reagent was decomposed with 5% aqueous potassium hydrogen sulfate. The mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography with 3:1 to 1:1 hexane/ethyl acetate to give 1.16 g of the title compound (64%).

Workup

  1. temperatureunder reflux
  2. additionAfter the addition
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography with 3:1 to 1:1 hexane/ethyl acetate

Sources & evidence

ORD record
ord-2ec2bcbb0bc540d38d6cd1b8f1eddfb4
Source dataset
uspto-grants-1998_02
Patent number
US05719152

Reaction notes

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