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

HRID 1093973

Reaction equation

HRID 1093973 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-d73769b6873c49feb8d2191713e330e3
Source dataset
uspto-grants-2012_03
Patent number
US08133889B2

Linked notes

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