Methanol → tert-Butyl (2-hydroxyethyl)phenylcarbamate

HRID 2269650Notes

Reaction equation

HRID 2269650 reaction equation
C1COCC1.[BH4-].[Li+].C[O:9][C:10](=O)[CH2:11][N:12]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].CO>O>[C:13]([N:12]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[CH2:11][CH2:10][OH:9])([O:15][C:16]([CH3:18])([CH3:19])[CH3:17])=[O:14]

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 4148881Lithium borohydrideHCID 22590373HCID 22590373, compound

Product 1

HCID 24720895tert-Butyl (2-hydroxyethyl)phenylcarbamateYield 35.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a THF solution containing 0.30 g of lithium borohydride, 1.30 g of N-(tert-butoxycarbonyl)phenylglycine methyl ester was added under ice cooling. To the resultant solution, methanol was added dropwise under ice cooling and stirred overnight at room temperature. Water was added to the reaction mixture, extracted with ethyl acetate. The organic layer was washed with water and saturated sodium chloride aqueous solution, successively, and dried over anhydrous sodium sulfate. The dried solution was evaporated under reduced pressure and the obtained residue was subjected to a silica gel column chromatography (hexane:ether=1:1) to give 0.41 g of the title compound.

Workup

  1. additionwas added under ice cooling
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated sodium chloride aqueous solution
  4. dry with materialsuccessively, and dried over anhydrous sodium sulfate
  5. customThe dried solution was evaporated under reduced pressure

Sources & evidence

ORD record
ord-63fbacd4783f4b8a98361e9f7fe80c99
Source dataset
uspto-grants-2001_12
Patent number
US06329502B1

Reaction notes

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