Methanol → tert-Butyl [4-(hydroxymethyl)benzyl]carbamate

HRID 2080781Notes

Reaction equation

HRID 2080781 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[CH:6][CH:5]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].CO.C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>C1COCC1>[C:15]([O:14][C:12](=[O:13])[NH:11][CH2:10][C:7]1[CH:6]=[CH:5][C:4]([CH2:3][OH:2])=[CH:9][CH:8]=1)([CH3:18])([CH3:16])[CH3:17]

Participants

6

Reactant 4

HCID 887MethanolHCID 9855836Potassium sodium tartarateHCID 14221817Methyl 4-((((1,1-dimethylethoxy)carbonyl)amino)methyl)benzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 2794813tert-Butyl [4-(hydroxymethyl)benzyl]carbamateYield 91.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound (35.7 g) obtained in Example 23-1 was dissolved in anhydrous THF (800 ml) and added with Lithium aluminum hydride (10.2 g) in an ice bath and the whole was stirred for 2 days under a nitrogen atmosphere. After completion of the reaction, methanol and then an aqueous sodium potassium tartrate solution were added thereto and the whole was stirred overnight. The resultant was subjected to extraction with chloroform and washed with saturated saline solution. The organic layer was dried with anhydrous sodium sulfate. The solvent was distilled off, thereby obtaining the subject compound (29.2 g) as a colorless crystal.

Workup

  1. stirringthe whole was stirred overnight
  2. extractionThe resultant was subjected to extraction with chloroform
  3. washwashed with saturated saline solution
  4. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  5. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-6903c4f168a24aca83dfa75ac1e8a1ee
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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