Tetramethylammonium fluoride → Tert-butyl 3-(5-chloro-2-hydroxyphenyl)azetidine-1-carboxylate

HRID 1692274

Reaction equation

HRID 1692274 reaction equation
[Si]([O:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[CH:16]1[CH2:19][N:18]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:17]1)(C(C)(C)C)(C)C.[F-].C[N+](C)(C)C>O1CCCC1>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[C:10]([CH:16]2[CH2:17][N:18]([C:20]([O:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[O:21])[CH2:19]2)[CH:11]=1

Participants

4

Reactant 2

HCID 67803Tetramethylammonium fluorideHCID 59436503tert-Butyl3-(2-{[tert-butyl(dimethyl)silyl]oxy)-5-chlorophenyl)azetidine-1-carboxylate

Product 1

HCID 59436608Tert-butyl 3-(5-chloro-2-hydroxyphenyl)azetidine-1-carboxylateYield 38%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-Butyl 3-(2-{[tert-butyl(dimethyl)silyl]oxy}-5-chlorophenyl)azetidine-1-carboxylate (Preparation 238, 3.1 g, 7.79 mmol) in tetrahydrofuran (80 ml) was added tetramethylammonium fluoride (1.0 g, 10.74 mmol). The mixture was stirred at room temperature for 18 hours before concentrating in vacuo. The residue was partitioned between tert-butyl methyl ether (100 ml) and aqueous sodium hydroxide solution. The organics were dried over sodium sulfate, filtered and evaporated in vacuo to give a reddish brown oil, 2.33 g. This was purified by column chromatography (100 g of silica) eluting with heptane:ethyl acetate (6:4, by volume) to afford the title compound as a reddish brown gum, 850 mg, 38% yield.

Workup

  1. concentrationbefore concentrating in vacuo
  2. customThe residue was partitioned between tert-butyl methyl ether (100 ml) and aqueous sodium hydroxide solution
  3. dry with materialThe organics were dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customto give a reddish brown oil, 2.33 g
  7. customThis was purified by column chromatography (100 g of silica)
  8. washeluting with heptane:ethyl acetate (6:4, by volume)

Sources & evidence

ORD record
ord-06238cd149fa435eb08dc2e15e1aa44e
Source dataset
uspto-grants-2012_04
Patent number
US08153814B2

Linked notes

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