Nitrogen → HCID 66929264, compound

HRID 42804Notes

Reaction equation

HRID 42804 reaction equation
N#N.C([SiH2][O:8][C:9](C)(C)[C:10]1[CH:15]=[CH:14][N:13]=[C:12]([C:16]2([CH3:21])[O:20][CH2:19][CH2:18][O:17]2)[CH:11]=1)(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.CC(=O)OCC>[CH3:21][C:16]1([C:12]2[CH:11]=[C:10]([CH2:9][OH:8])[CH:15]=[CH:14][N:13]=2)[O:17][CH2:18][CH2:19][O:20]1

Participants

6

Reactant 3

HCID 947NitrogenHCID 2724141Tetrabutylammonium FluorideHCID 131730003HCID 131730003, compound

Product 1

HCID 66929264HCID 66929264, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 4-(tert-butyl-dimethyl-silanyloxymethyl)-2-(2-methyl-[1,3]dioxolan-2-yl)-pyridine (840 mg, 2.71 mmol) in dry THF (15 mL) was treated at 0° C. with TBAF (4.70 mL of a 1M solution in THF, 4.70 mmol). The reaction mixture was stirred at 0° C. for 5 min and at rt for 1.5 h. The mixture was then diluted with EA (10 mL), washed with brine (3×10 mL), dried over MgSO4, filtered and concentrated under reduced pressure. Purification of the residue by FC (5:1 to 1:3 hept-EA) gave the title compound as a yellow oil. TLC:rf (1:2 hept-EA)=0.10. LC-MS-conditions 02: tR=0.33 min; [M+H]+=196.54.

Workup

  1. washwashed with brine (3×10 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customPurification of the residue by FC (5:1 to 1:3 hept-EA)

Sources & evidence

ORD record
ord-b91b365a5d9f4cdd9edba7e7761d2d4b
Source dataset
uspto-grants-2013_09
Patent number
US08536209B2

Reaction notes

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