Tetrabutylammonium Fluoride → 4-(1H-Pyrrol-3-ylmethyl)-morpholine

HRID 241708

Reaction equation

HRID 241708 reaction equation
C([Si](C(C)C)(C(C)C)[N:5]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[CH:6]1)(C)C.[N+](CCCC)(CCCC)(CCCC)CCCC.[F-]>C1COCC1>[NH:5]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]2[CH2:12][CH2:13][O:14][CH2:15][CH2:16]2)=[CH:6]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 666367604-(1-Triisopropylsilanyl-1H-pyrrol-3-ylmethyl)-morpholine

Product 1

HCID 575870184-(1H-Pyrrol-3-ylmethyl)-morpholine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of the compound obtained in Step A (75 mmoles) in THF (100 ml) there is added, dropwise, at 0° C., Bu4NF 1.0M in THF (75.0 mmoles). After stiffing at 0° C. for one hour, the solution is poured onto ice and is then extracted with DCM. The organic phases are combined and then washed with saturated aqueous NaCl solution, dried over sodium sulphate, filtered and evaporated to dryness to yield the title product, which is used directly in the next Step.

Workup

  1. customat 0° C.
  2. additionthe solution is poured onto ice
  3. extractionis then extracted with DCM
  4. washwashed with saturated aqueous NaCl solution
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-e634878a2a9d4cf187ed6a294a2f3208
Source dataset
uspto-grants-2014_02
Patent number
US08653073B2

Linked notes

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