Toluene → tert-Butyl 3-(hydroxymethyl)benzylcarbamate

HRID 2171676Notes

Reaction equation

HRID 2171676 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[C:12]([CH:17]=[CH:18][CH:19]=1)[C:13](OC)=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(C)C=CC=CC=1.[H-].COCCO[Al+]OCCOC.[Na+].[H-].[OH-].[Na+]>C(Cl)(Cl)Cl>[OH:14][CH2:13][C:12]1[CH:11]=[C:10]([CH:19]=[CH:18][CH:17]=1)[CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:4])[CH3:2]

Participants

6

Reactant 4

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydrideHCID 22710582Methyl 3-(((tert-butoxycarbonyl)amino)methyl)benzoate

Product 1

HCID 2794814tert-Butyl 3-(hydroxymethyl)benzylcarbamateYield 99.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

Methyl 3-{[(tert-butoxycarbonyl)amino]methyl}benzoate (4.6 g) was mixed with toluene (50 ml), followed by cooling to 0° C. Sodium bis(2-methoxyethoxy)aluminum hydride (65% toluene solution) (20 g) was added dropwise over 30 minutes, followed by stirring at 0° C. for 1 hour. A 1M aqueous NaOH solution (30 ml) was added dropwise to the reaction mixture, and CHCl3 was then added thereto. The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/EtOAc) to obtain tert-butyl [3-(hydroxymethyl)benzyl]carbamate (4.1 g).

Workup

  1. additionwas then added
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-ee32e21037324adda73bf60d55474fa8
Source dataset
uspto-grants-2015_06
Patent number
US09051283B2

Reaction notes

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