2,6-Lutidine → Dodecylamine

HRID 2228657Notes

Reaction equation

HRID 2228657 reaction equation
[Si](OS(C(F)(F)F)(=O)=O)([C:4]([CH3:7])([CH3:6])C)(C)C.[N:16]1[C:21](C)=[CH:20][CH:19]=[CH:18][C:17]=1[CH3:23].[CH3:24][CH2:25][CH2:26]C[N+](CCCC)(CCCC)CCCC.[F-]>C(Cl)Cl.C1COCC1>[CH3:24][CH2:25][CH2:26][CH2:6][CH2:4][CH2:7][CH2:23][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][NH2:16]

Participants

6

Reactant 3

HCID 79372,6-LutidineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 2724141Tetrabutylammonium Fluoride

Product 1

HCID 13583Dodecylamine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lactol 8 [for the synthesis of 8, see Prostaglandins 1983, 25(3), 311] is condensed with Ph3P+CH2OCH3 Cl− in THF in the presence of potassium t-butoxide to afford enol ether 9. Conversion of 9 to lactol 10 is effected using HCl in aqueous isopropanol. Reaction of 10 with Ph3P+(CH2)3CO2H Br− in THF in the presence of potassium t-butoxide, followed by isolation of the product olefin acid and esterification with isopropyl iodide in the acetone in presence of DBU, provides ester 11. Treatment of 11 with TBSOTf and 2,6-lutidine in CH2Cl2, followed by addition of TBAF in THF, yields amine 12. DPA-mediated coupling of 12 with acid 6 gives amide 13, which is deprotected with TBAF in THF to afford III after chromatographic separation of the carbon 15 diastereomers.

Sources & evidence

ORD record
ord-0d231845f9bb483e8abf69d5a58102e9
Source dataset
uspto-grants-2002_07
Patent number
US06417228B1

Reaction notes

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