Water → t-Butyl N-[5-(hydroxymethyl)-2-methoxybenzyl]carbamate

HRID 2222446Notes

Reaction equation

HRID 2222446 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([O:18][CH3:19])=[C:7]([CH:17]=1)[CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:2].[BH4-].[Na+].O>C(O)C.O1CCCC1>[OH:2][CH2:1][C:3]1[CH:4]=[CH:5][C:6]([O:18][CH3:19])=[C:7]([CH:17]=1)[CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13]

Participants

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 22493931Tert-butyl (5-formyl-2-methoxybenzyl)carbamate

Product 1

HCID 59712518t-Butyl N-[5-(hydroxymethyl)-2-methoxybenzyl]carbamateYield 91%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.8 g of t-butyl N-(5-formyl-2-methoxybenzyl)carbamate was dissolved in 12 ml of ethanol and 6 ml of tetrahydrofuran, and 0.15 g of sodium borohydride was added. After stirring at room temperature overnight, water was added and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and the solvent was removed. The residue was purified by silica gel column chromatography, to give 1.65 g of the title compound from the 1:1 hexane-ethyl acetate fraction.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. customthe solvent was removed
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f105aae978074a11baff03227fa0f908
Source dataset
uspto-grants-2008_05
Patent number
US07371777B2

Reaction notes

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