HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 1715374
Notes
Print preview

Reaction equation

HRID 1715374 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 8028
Tetrahydrofuran
Solvent

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-de32258c19524648a929bce992b764f4
Source dataset
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07799819B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes