4-Toluenesulfonyl chloride → HCID 54383241, compound

HRID 234652Notes

Reaction equation

HRID 234652 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C@H:7](O)[CH3:8])=[CH:3][CH:2]=1.C([Li])CCC.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.C(NC(C)C)(C)C.[CH3:33][C:34]([C:36]12[CH2:45][CH:40]3[CH2:41][CH:42]([CH2:44][CH:38]([CH2:39]3)[CH2:37]1)[CH2:43]2)=[O:35]>C1COCC1.CCCCCC>[C:36]12([C:34](=[O:35])[CH2:33][C@H:7]([C:4]3[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=3)[CH3:8])[CH2:43][CH:42]3[CH2:41][CH:40]([CH2:39][CH:38]([CH2:44]3)[CH2:37]1)[CH2:45]2

Participants

8

Reactant 5

HCID 73974-Toluenesulfonyl chlorideHCID 7912DiisopropylamineHCID 123126Methyl tricyclo(3.3.1.13,7)dec-1-yl ketoneHCID 11804747(1R)-1-(pyridin-4-yl)ethan-1-olHCID 178418339Butyllithium2×

Product 1

HCID 54383241HCID 54383241, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent2×

Procedure

The method followed that described in Example 9 but using (+)-(R)-1-(4-pyridyl)ethanol (1.84 g, 15.0 mmol) in THF (80 ml), butyllithium (1.6M; 9.4 ml, 15.0 mmol) in hexane, p-toluenesulfonyl chloride (2.86 g, 15.0 mmol), diisopropylamine (6.31 ml, 45.0 mmol) in THF (120 ml), butyllithium (1.6M; 28.12 ml, 45.0 mmol) in hexane and 1-adamantyl methyl ketone (8.0 g, 45 mmol). Chromatography, on elution with petrol-ether-triethylamine 100:50:1 gave the title compound (722 mg, 17%), which crystallised from hexane, m.p. 48°-49° C.; [α]D -6.6° (c 1.0, MeOH). IR, NMR and MS data were the same as given in Example 14.

Workup

  1. washChromatography, on elution with petrol-ether-triethylamine 100:50:1

Sources & evidence

ORD record
ord-094bfc5e0cb04b82b87f0adbe057e7df
Source dataset
uspto-grants-1997_01
Patent number
US05595995

Reaction notes

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