2-Methyl-2-butene → HCID 53802001, compound

HRID 726761Notes

Reaction equation

HRID 726761 reaction equation
Cl([O-])=O.[Na+].[OH2:5].OP([O-])(O)=O.[Na+].[CH:12]1([O:17][C:18]2[CH:19]=[C:20]([C@@H:26]([C:34]3[CH:39]=[CH:38][C:37]([CH2:40][CH:41]=[O:42])=[CH:36][CH:35]=3)[CH2:27][C:28]3[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=3)[CH:21]=[CH:22][C:23]=2[O:24][CH3:25])[CH2:16][CH2:15][CH2:14][CH2:13]1.CC(=CC)C>O.CC(O)(C)C.C(O)(=O)C>[CH:12]1([O:17][C:18]2[CH:19]=[C:20]([C@@H:26]([C:34]3[CH:35]=[CH:36][C:37]([CH2:40][C:41]([OH:5])=[O:42])=[CH:38][CH:39]=3)[CH2:27][C:28]3[CH:29]=[CH:30][N:31]=[CH:32][CH:33]=3)[CH:21]=[CH:22][C:23]=2[O:24][CH3:25])[CH2:13][CH2:14][CH2:15][CH2:16]1

Participants

8

Reactant 4

HCID 105532-Methyl-2-buteneHCID 516949Sodium Phosphate, Monobasic, MonohydrateHCID 23668197Sodium ChloriteHCID 54132651HCID 54132651, compound

Product 1

HCID 53802001HCID 53802001, compoundYield 83%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

A solution of sodium chlorite (80%; 131 mg, 1.16 mmol) and sodium phosphate monobasic monohydrate (160 mg, 1.16 mmol) in water (1.1 mL) was added to a solution of (R)-4-[1-(3-cyclopentyloxy-4-methoxyphenyl)-2-(4-pyridyl)ethyl]phenylacetaldehyde from Step 5 (371 mg, 0.893 mmol) and 2-methyl-2-butene (665 μL, 6.25 mmol) in t-BuOH (8 mL). The reaction mixture was stirred at room temperature for 1.5 h before 25% aqueous NH4OAc buffer was added (a few drops of acetic acid were necessary to bring the pH at 7). The mixture was then extracted with EtOAc (2×), and the combined organics were washed successively with 25% aqueous NH4OAc buffer, water and brine, dried (MgSO4) and concentrated. The residue was purified by column chromatography on silica (EtOAc containing 0.5% AcOH). Residual AcOH was co-evaporated with toluene (2×) to afford the title compound as a white foam (319 mg, 83%). 1H NMR (400 MHz, acetone-d6): δ 1.50-1.61 (m, 2H), 1.63-1.88 (m., 6H), 3.40 (d; 2H), 3.54 (s, 2H), 3.70 (s, 3H), 4.34 (t, J=8 Hz, 1H), 4.75 (m, 1H), 6.78 (m, 2H), 6.90 (s, 1H), 7.15 (d, J=6 Hz, 2H), 7.20 (d, J=8 Hz, 2H), 7.30 (d, J=8 Hz, 2H), 8.33 (d, J=5 Hz, 2H).

Workup

  1. extractionThe mixture was then extracted with EtOAc (2×)
  2. washthe combined organics were washed successively with 25% aqueous NH4OAc buffer, water and brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica (EtOAc containing 0.5% AcOH)

Sources & evidence

ORD record
ord-6bb56407e91947fa87c1b73373446027
Source dataset
uspto-grants-1998_01
Patent number
US05710170

Reaction notes

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