HCID 69079353, compound → HCID 69077265, compound

HRID 1987159Notes

Reaction equation

HRID 1987159 reaction equation
[C:1]([CH2:8][C:9](=[O:19])[CH:10]([NH2:18])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH3:20][Mg]Br>C(Cl)Cl>[C:1]([CH2:8][C:9]([CH3:20])([OH:19])[CH:10]([NH2:18])[CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 69079353HCID 69079353, compoundHCID 178418573HCID 178418573, compound2×

Product 1

HCID 69077265HCID 69077265, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Grignard Addition A solution of Boc-3-amino-4-phenyl-2-butanone (0.5 g, 1.9 mmol) in 100 mL methylene chloride was cooled to −78° C. and treated with methyl magnesium bromide (1.39 mL of a 3.0M solution, 4.2 mmol). The reaction was warmed to ambient temperature and stirred for 14 hours. The reaction was charged with additional methyl magnesium bromide (1.39 mL of a 3.0 M solution, 4.2 mmol) and stirred at ambient temperature for 5 hours. The reaction was quenched with ammonium chloride solution and partitioned between water and ethyl acetate. The organics were washed with water (3×), brine, dried over sodium sulfate, filtered and evaporated in vactio. Purification by flash column chromatography (20-35% ethyl acetate/hexanes) gave Boc-3-amino-2-methyl-4-phenylbutan-2-ol as a white solid: 1H NMR (400 MHz, CDCl3) δ 7.25 (m, 5H), 4.52 (m, 1H), 3.69 (m, 1H), 3.09 (dd, J=14.1, 3.3 Hz, 1H), 2.61 (t, J=12.0 Hz, 1H), 2.39 (s, 1H), 1.30 (m, 15H). Step B: Deprotection

Workup

  1. stirringstirred at ambient temperature for 5 hours
  2. customThe reaction was quenched with ammonium chloride solution
  3. custompartitioned between water and ethyl acetate
  4. washThe organics were washed with water (3×), brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated in vactio
  8. customPurification by flash column chromatography (20-35% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-34fa0345be424c0e8738a27809120126
Source dataset
uspto-grants-2009_06
Patent number
US07550481B2

Reaction notes

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