Methanol → (R)-[1-(3-ethoxy-4-methoxy-phenyl)-3-hydroxy-3-methyl-butyl]-carbamic acid tert-butyl ester

HRID 1797249Notes

Reaction equation

HRID 1797249 reaction equation
[C:1]([O:5][C:6](=[O:24])[NH:7][C@@H:8]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH2:22][CH3:23])[CH:14]=1)[CH2:9][C:10](=[O:12])[CH3:11])([CH3:4])([CH3:3])[CH3:2].[CH3:25][Li].CO>C1COCC1>[C:1]([O:5][C:6](=[O:24])[NH:7][C@@H:8]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH2:22][CH3:23])[CH:14]=1)[CH2:9][C:10]([OH:12])([CH3:25])[CH3:11])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 887MethanolHCID 67175757(1R)-[1-(3-ethoxy-4-methoxy-phenyl)-3-oxo-butyl]-carbamic acid tert-butyl esterHCID 178418348HCID 178418348, compound

Product 1

HCID 68687518(R)-[1-(3-ethoxy-4-methoxy-phenyl)-3-hydroxy-3-methyl-butyl]-carbamic acid tert-butyl esterYield 14.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (1R)-[1-(3-ethoxy-4-methoxy-phenyl)-3-oxo-butyl]-carbamic acid tert-butyl ester (1 g, 3 mmol) in THF (10 mL) was added a solution of methyl lithium (4 mL, 3M, 12 mmol) at 0° C. To the mixture was added methanol (5 mL). The residue was extracted with ethyl acetate (50 mL) and NH4Cl (sat, 25 mL). The organic layer was washed with brine (100 mL) and dried over MgSO4. The solvent was removed in vacuo. The residue was purified with preparative HPLC to give (R)-[1-(3-ethoxy-4-methoxy-phenyl)-3-hydroxy-3-methyl-butyl]-carbamic acid tert-butyl ester (150 mg, 14% yield).

Workup

  1. extractionThe residue was extracted with ethyl acetate (50 mL) and NH4Cl (sat, 25 mL)
  2. washThe organic layer was washed with brine (100 mL)
  3. dry with materialdried over MgSO4
  4. customThe solvent was removed in vacuo
  5. customThe residue was purified with preparative HPLC

Sources & evidence

ORD record
ord-f3cc6338126e4ca1b48cc1abeec077a4
Source dataset
uspto-grants-2006_04
Patent number
US07034052B2

Reaction notes

Loading…