Tetrahydrofuran → HCID 25114168, compound

HRID 1894685Notes

Reaction equation

HRID 1894685 reaction equation
O1CCCC1.[CH2:6]([Sn:10]([CH2:17][CH2:18][CH2:19][CH3:20])([CH2:13][CH2:14][CH2:15][CH3:16])[C:11]#[CH:12])[CH2:7][CH2:8][CH3:9].[N+:21]([CH2:24][CH2:25][C:26]1[CH:39]=[CH:38][C:29]([CH2:30][O:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=2)=[CH:28][CH:27]=1)([O-:23])=O.C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O>CN(C)C1C=CN=CC=1.O.C(OCC)(=O)C>[CH2:17]([Sn:10]([CH2:13][CH2:14][CH2:15][CH3:16])([CH2:6][CH2:7][CH2:8][CH3:9])[C:11]1[O:23][N:21]=[C:24]([CH2:25][C:26]2[CH:39]=[CH:38][C:29]([CH2:30][O:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=3)=[CH:28][CH:27]=2)[CH:12]=1)[CH2:18][CH2:19][CH3:20]

Participants

8

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 90495Di-tert-butyl dicarbonateHCID 621176EthynyltributyltinHCID 580762662-((4-(2-Nitroethyl)benzyl)oxy)pyridine

Product 1

HCID 25114168HCID 25114168, compoundYield 100.2%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a tetrahydrofuran solution (90 mL) of tri-n-butylethynyltin (3 g), 2-(4-(2-nitro-ethyl)-benzyloxy)-pyridine (4.9 g) described in Manufacturing Example 1-1-4, and 4-dimethylaminopyridine (116 mg) was added a tetrahydrofuran solution (30 mL) of di-tert-butyl dicarbonate (7.3 g), which was stirred for 15 hours at room temperature. Ethyl acetate and water were added to this mixture. The organic layer was separated, washed with water and saturated saline, dried over anhydrous magnesium sulfate, and filtered. The filtrate was adsorbed to silica gel, and then purified by silica gel column chromatography (heptane:ethyl acetate=4:1) to obtain the title compound (5.3 g).

Workup

  1. customThe organic layer was separated
  2. washwashed with water and saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. custompurified by silica gel column chromatography (heptane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-3a8f1203a3494a4c952462996666d4ca
Source dataset
uspto-grants-2013_08
Patent number
US08513287B2

Reaction notes

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