Aluminium lithium hydride → tert-Butyl 3-(hydroxymethyl)benzyl(methyl)carbamate

HRID 2355282Notes

Reaction equation

HRID 2355282 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH3:12])[CH:5]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[C:16]([O:15][C:13](=[O:14])[N:11]([CH2:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([CH2:3][OH:2])[CH:5]=1)[CH3:12])([CH3:19])([CH3:17])[CH3:18]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 59700597Methyl 3-(((tert-butoxycarbonyl)(methyl)amino)methyl)benzoate

Product 1

HCID 18470938tert-Butyl 3-(hydroxymethyl)benzyl(methyl)carbamateYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Dissolve 3-[(tert-butoxycarbonyl-methyl-amino)-methyl]-benzoic acid methyl ester (1.70 g, 6.1 mmol) in tetrahydrofuran (60 mL) at 0° C. Add a 1M solution of lithium aluminum hydride in tetrahydrofuran (8 mL, 8 mmol) dropwise and stir for 2 hrs. Quench the reaction with water (3 mL), 5N sodium hydroxide solution (3 mL) and more water (9 mL), filter and concentrate. Purify the residue by chromatography (silica gel) eluting with 40-60% ethyl acetate/hexanes to provide the title compound (1.42 g, 93%).

Workup

  1. customQuench
  2. customthe reaction with water (3 mL), 5N sodium hydroxide solution (3 mL) and more water (9 mL)
  3. filtrationfilter
  4. concentrationconcentrate
  5. customPurify the residue by chromatography (silica gel)
  6. washeluting with 40-60% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-74b771b0f1ee4432b1714dfdda0ebe63
Source dataset
uspto-grants-2010_07
Patent number
US07754742B2

Reaction notes

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