4-Pyridinecarboxaldehyde → HCID 10635548, compound

HRID 234655Notes

Reaction equation

HRID 234655 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH:7]=O)=[CH:3][CH:2]=1.C([Li])CCC.[CH3:14][C:15]([C:17]12[CH2:26][CH:21]3[CH2:22][CH:23]([CH2:25][CH:19]([CH2:20]3)[CH2:18]1)[CH2:24]2)=[O:16]>C1COCC1.C(NC(C)C)(C)C>[C:17]12([C:15](=[O:16])/[CH:14]=[CH:7]/[C:4]3[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=3)[CH2:24][CH:23]3[CH2:22][CH:21]([CH2:20][CH:19]([CH2:25]3)[CH2:18]1)[CH2:26]2

Participants

6

Reactant 3

HCID 133894-PyridinecarboxaldehydeHCID 123126Methyl tricyclo(3.3.1.13,7)dec-1-yl ketoneHCID 178418339Butyllithium

Product 1

HCID 10635548HCID 10635548, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 7912DiisopropylamineSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

The method essentially followed that described in Example 17a but using 4-pyridinecarboxaldehyde (0.48 ml, 5.0 mmol) in THF (6 ml), diisopropylamine in THF (20 ml), butyllithium (3.13 g, 5.0 mmol) and 1-adamantyl methyl ketone (0.48 ml, 5.0 mmol). Chromatography, on elution with petrol-ether-triethylamine 100:100:1, gave the title compound (881 mg, 66%), which crystallised from hexane, m.p. 128°-129° C., IR νmax 1690 cm-1 ; 1H-NMR (CDCl3) δ1.72-1.89 (12H, adamantyl CH2) 2.12 (3H, s, adamantyl CH), 7.36 (1H, d, J 15.6 Hz, COCHCH), 7.56 (1H, d, J 15.6 Hz, COCHCH), 7.71 (2H, d, J 5.5 Hz, Py 3-H and 5-H), 8.71 (2H, d, J 5.5 Hz, Py 2-H and 6-H); MS m/z 267 (M+). Anal. Calcd: C, 80.86; H, 7.92; N, 5.24. Found: C, 80.96; H, 8.13; N, 5.04 %.

Workup

  1. washChromatography, on elution with petrol-ether-triethylamine 100:100:1

Sources & evidence

ORD record
ord-6894ebd707f646f8be9d439ecd0a2be1
Source dataset
uspto-grants-1997_01
Patent number
US05595995

Reaction notes

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