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

HRID 44253Notes

Reaction equation

HRID 44253 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×

Conditions

Temperature
0 °C

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 stirring 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-7cecaa6b366145c09e288eccc4d1f28e
Source dataset
uspto-grants-2013_09
Patent number
US08541412B2

Reaction notes

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