Tetrabutylammonium Fluoride → (S)-N-{1-[4-(3-Hydroxy-azetidin-1-yl)-phenyl]ethyl}-acetamide

HRID 40500

Reaction equation

HRID 40500 reaction equation
C([Si](C)(C)[O:6][CH:7]1[CH2:10][N:9]([C:11]2[CH:16]=[CH:15][C:14]([C@@H:17]([NH:19][C:20](=[O:22])[CH3:21])[CH3:18])=[CH:13][CH:12]=2)[CH2:8]1)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[OH:6][CH:7]1[CH2:8][N:9]([C:11]2[CH:12]=[CH:13][C:14]([C@@H:17]([NH:19][C:20](=[O:22])[CH3:21])[CH3:18])=[CH:15][CH:16]=2)[CH2:10]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86689004(S)-N-(1-{4-[3-(tert-Butyl-dimethyl-silanyloxy)-azetidin-1-yl]-phenyl}-ethyl)-acetamide

Product 1

HCID 86689005(S)-N-{1-[4-(3-Hydroxy-azetidin-1-yl)-phenyl]ethyl}-acetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

2.6 g (7.46 mmol) (S)—N-(1-{4-[3-(tert-Butyl-dimethyl-silanyloxy)-azetidin-1-yl]-phenyl}-ethyl)-acetamide (IV.1) are added to 20 mL THF and the mixture is cooled to 5° C. 14.9 mL (14.9 mmol) tetrabutylammonium fluoride (1 N in THF) are added and the mixture is allowed to warm to rt. Stirring is continued for 1 h and the solvent is removed in vacuo. The residue is purified by column chromatography (silica gel; DCM:MeOH; gradient 9:1→8:2) to yield the desired product.

Workup

  1. temperatureto warm to rt
  2. customthe solvent is removed in vacuo
  3. customThe residue is purified by column chromatography (silica gel; DCM:MeOH; gradient 9:1→8:2)

Sources & evidence

ORD record
ord-fd014b637aa44552beae9feea3f513c9
Source dataset
uspto-grants-2013_09
Patent number
US08530461B2

Linked notes

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