Methyl iodide → HCID 23355091, compound

HRID 234650Notes

Reaction equation

HRID 234650 reaction equation
[CH:1](NC(C)C)(C)C.C([Li])CCC.[C:13]12([C:23](=[O:32])[CH2:24][CH2:25][C:26]3[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=3)[CH2:22][CH:17]3[CH2:18][CH:19]([CH2:21][CH:15]([CH2:16]3)[CH2:14]1)[CH2:20]2.CI>C1COCC1.CCCCCC>[C:13]12([C:23](=[O:32])[CH:24]([CH3:1])[CH2:25][C:26]3[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=3)[CH2:22][CH:17]3[CH2:18][CH:19]([CH2:21][CH:15]([CH2:16]3)[CH2:14]1)[CH2:20]2

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 7912DiisopropylamineHCID 23355088HCID 23355088, compoundHCID 178418339Butyllithium

Product 1

HCID 23355091HCID 23355091, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of diisopropylamine (0.42 ml, 3.0 mmol) in THF (10 ml) at 0° C. was added butyllithium (1.6M; 1.87 ml, 3.0 ml) in hexane followed after 5 minutes by a solution of 1-(1-adamantyl)-3-(3-pyridyl)propan-1-one in THF (8 ml). After stirring for a further 20 min at 0° C., methyl iodide (0.19 ml, 3.0 mmol) was added dropwise and the solution was allowed to attain room temperature. After 1 hr the mixture was partitioned between ether and water. The ether extracts were dried (Na2CO3) and concentrated. Chromatography on elution with petrol-ether-triethylamine 100:50:1 afforded the title compound (0.62g, 73%), which crystallised from pentane, m.p 69-70 C; IR νmax 1696 cm-1 ; 1H-NMR (CDCl3) δ1.06 (3H,d,J 6.7 Hz, CHCH3) 1.51-1.72 (12H, m, adamantyl CH2), 1.96 (3H, s, adamantyl CH), 2.57 and 2.92 (2H, m, CHCH2), 3.28 (1H, m, CHCH3), 7.18 (1H, m, Py 5-H), 7.43 (1H, m, Py 4-H), 8.43 (2H, m, Py 6-H and 2-H); MS m/z 283 (M+). Anal. Calcd: C, 80.52; H, 8.89; N, 4.94. Found: C, 80.56; H, 8.95; N, 4.91%.

Workup

  1. customto attain room temperature
  2. customAfter 1 hr the mixture was partitioned between ether and water
  3. dry with materialThe ether extracts were dried (Na2CO3)
  4. concentrationconcentrated
  5. washChromatography on elution with petrol-ether-triethylamine 100:50:1

Sources & evidence

ORD record
ord-36bb212adf3649e288375c9cfdf63642
Source dataset
uspto-grants-1997_01
Patent number
US05595995

Reaction notes

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