Water → HCID 57714155, compound

HRID 1984271Notes

Reaction equation

HRID 1984271 reaction equation
[C:1]([NH:20][C@H:21]([CH2:25][CH3:26])[C:22](=[O:24])[CH3:23])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:27][Mg]I.O>CCOCC>[CH3:23][C:22]([OH:24])([C@H:21]([NH:20][C:1]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:25][CH3:26])[CH3:27]

Participants

5

Reactant 3

HCID 962WaterHCID 57714165(3R)-3-(Trityl-amino)-pentan-2-oneHCID 178418373HCID 178418373, compound

Product 1

HCID 57714155HCID 57714155, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of (3R)-3-(trityl-amino)-pentan-2-one (0.87 g, 1 eq, 2.54 mmol) in Et2O (100 mL) under an argon atmosphere at room temperature, was added methylmagnesium iodide (3 M in ether, 2.54 mL, 3 eq, 7.62 mmol) dropwise. The solution was placed in a preheated oil bath at 45° C. and refluxed at this temperature for 16 h. The mixture was recooled to 0° C., H2O (100 mL) added, the solution filtered through Celite, and the Celite washed with more Et2O (50 mL). The combined organic phase was separated, the aqueous phase was extracted with Et2O (2×50 mL), and the combined organic phase washed with brine (50 mL), dried (NgSO4) and evaporated in vacuo. The residue was purified by silica gel colunm chromatography, eluted with hexane:ether (100:0→90:10) to afford the title compound as a light yellow oil. Yield: 0.21 g (23%). 1H-NMR (d6-DMSO, 250 MHz): δ 0.26 (t, J=7.42 Hz, —NHCH (CH2CH3)CH(CH3)OH), 1.00 & 1.25 (2×s, 6H, —NHCH(CH2CH3) C(CH 3)2 OH), 0.72-1.43 (m, 2H, —NHCH(CH2CH3)C(CH3)2OH), 1.84 (m, 1H, —NHCH (CH2CH3)C(CH3)2OH), 2.90 (m, 1H, —NHCH(CH2CH3)C(CH3)2OH), 4.32 (s, 1H, —NHCH(CH2CH3) C(CH3)2OH), 7.17-7.46 (m, 15H, 3×Ph).

Workup

  1. customThe solution was placed in a preheated oil bath at 45° C.
  2. temperaturerefluxed at this temperature for 16 h
  3. customwas recooled to 0° C.
  4. filtrationthe solution filtered through Celite
  5. washthe Celite washed with more Et2O (50 mL)
  6. customThe combined organic phase was separated
  7. extractionthe aqueous phase was extracted with Et2O (2×50 mL)
  8. washthe combined organic phase washed with brine (50 mL)
  9. customdried (NgSO4)
  10. customevaporated in vacuo
  11. customThe residue was purified by silica gel colunm chromatography
  12. washeluted with hexane:ether (100:0→90:10)

Sources & evidence

ORD record
ord-c152c3aee1e2476fafd0d393a3e2fa99
Source dataset
uspto-grants-2009_06
Patent number
US07544689B2

Reaction notes

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