Ethanol → tert-Butyl 2-Hydroxy-2-(4-(hydroxymethyl)phenyl)ethyl(methyl)carbamate

HRID 23717Notes

Reaction equation

HRID 23717 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]([OH:20])[CH2:10][N:11]([CH3:19])[C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:5][CH:4]=1)=[O:2].C(O)C.[BH4-].[Na+]>C1COCC1>[OH:20][CH:9]([C:6]1[CH:7]=[CH:8][C:3]([CH2:1][OH:2])=[CH:4][CH:5]=1)[CH2:10][N:11]([CH3:19])[C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:15])[CH3:16]

Participants

5

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 22574298tert-Butyl 2-(4-Formylphenyl)-2-hydroxyethyl(methyl)carbamate

Product 1

HCID 22574345tert-Butyl 2-Hydroxy-2-(4-(hydroxymethyl)phenyl)ethyl(methyl)carbamateYield 99.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl 2-(4-formylphenyl)-2-hydroxyethyl(methyl)carbamate (1.808 g, 6.48 mmol) was dissolved in dry THF (50 ml) and absolute ethanol (10 ml) then cooled in an ice bath. Sodium borohydride (0.25 g, 6.61 mmol) was added then after 1 hr the solvent was evaporated. The residue was treated with satd. ammonium chloride solution (15 ml), water (35 ml) and chloroform (50 ml). The aqueous layer was extracted with additional chloroform (2×50 ml). The combined organics were washed with brine (30 ml), dried (magnesium sulfate), filtered and evaporated to afford the product as a white gum (1.82 g).

Workup

  1. customafter 1 hr the solvent was evaporated
  2. additionThe residue was treated with satd
  3. extractionThe aqueous layer was extracted with additional chloroform (2×50 ml)
  4. washThe combined organics were washed with brine (30 ml)
  5. dry with materialdried (magnesium sulfate)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-59bc4cf65fa34948a4afb82304f736fc
Source dataset
uspto-grants-2005_02
Patent number
US06852731B2

Reaction notes

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