Methyl iodide → HCID 178500372, compound

HRID 1713887Notes

Reaction equation

HRID 1713887 reaction equation
[CH:1]([N-]C(C)C)(C)C.[Li+].[Si:9]([O:16][C:17]1[CH:22]=[CH:21][C:20]([C@H:23]2[CH2:28][CH2:27][C@H:26]([CH:29]([CH3:34])[C:30]([O:32][CH3:33])=[O:31])[CH2:25][CH2:24]2)=[CH:19][CH:18]=1)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10].CI.[Cl-].[NH4+]>C1COCC1.C(OCC)(=O)C>[Si:9]([O:16][C:17]1[CH:18]=[CH:19][C:20]([C@H:23]2[CH2:24][CH2:25][C@H:26]([C:29]([CH3:1])([CH3:34])[C:30]([O:32][CH3:33])=[O:31])[CH2:27][CH2:28]2)=[CH:21][CH:22]=1)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:10])[CH3:11]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 2724682Lithium diisopropylamideHCID 178500454HCID 178500454, compound

Product 1

HCID 178500372HCID 178500372, compoundYield 87.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of lithium diisopropylamide (12.9 mmol) in THF (20 mL) was added dropwise to a stirred solution of methyl 2-[trans-4-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)cyclohexyl]-propanoate (4.42 g, 11.7 mmol) in THF (40 mL) at −78° C. under an argon atmosphere and the mixture was warmed to room temperature. The mixture was cooled to −78° C. and methyl iodide (0.92 mL, 14.7 mmol) was added dropwise. The reaction mixture was warmed to room temperature and stirred for 20 h. Saturated aqueous ammonium chloride (100 mL) and ethyl acetate were added sequentially, both in one portion. The organic layer was separated and washed with H2O and brine, dried (MgSO4) and concentrated in vacuo to leave an oil. The oil was purified by column chromatography, using a gradient of 0-15% ethyl acetate:isohexane was eluent, to give the title compound (4.0 g, 87%) as a colourless oil; 1H NMR δ 0.0 (6H, s), 0.8 (9H, s), 0.98 (6H, s), 1.0-1.1 (2H, m), 1.18-1.31 (2H, m), 1.45-1.56 (3H, m), 1.7-1.8 (2H, m), 2.15-2.28 (1H, m), 3.5 (3H, s), 6.55 (2H, d), 6.85 (2H, d).

Workup

  1. temperatureThe mixture was cooled to −78° C.
  2. temperatureThe reaction mixture was warmed to room temperature
  3. customThe organic layer was separated
  4. washwashed with H2O and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customto leave an oil
  8. customThe oil was purified by column chromatography

Sources & evidence

ORD record
ord-bb94b6ac589a431fb0ad03d6787d2007
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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