Tetramethylammonium fluoride → 2-Methyl-propane-2-sulfinic acid [1-(8-cyclopropylmethyl-1,4-dioxa-spiro[4.5]dec-8-yl)-2,2,2-trifluoro-ethyl]-amide

HRID 1948148Notes

Reaction equation

HRID 1948148 reaction equation
[CH:1]1([CH2:4][C:5]2([CH:15]=[N:16][S:17]([C:19]([CH3:22])([CH3:21])[CH3:20])=[O:18])[CH2:14][CH2:13][C:8]3([O:12][CH2:11][CH2:10][O:9]3)[CH2:7][CH2:6]2)[CH2:3][CH2:2]1.[F-].C[N+](C)(C)C.[F:29][C:30]([Si](C)(C)C)([F:32])[F:31]>O1CCCC1>[CH:1]1([CH2:4][C:5]2([CH:15]([NH:16][S:17]([C:19]([CH3:22])([CH3:21])[CH3:20])=[O:18])[C:30]([F:32])([F:31])[F:29])[CH2:14][CH2:13][C:8]3([O:12][CH2:11][CH2:10][O:9]3)[CH2:7][CH2:6]2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 67803Tetramethylammonium fluorideHCID 552549(Trifluoromethyl)trimethylsilaneHCID 67072583HCID 67072583, compound

Product 1

HCID 670727082-Methyl-propane-2-sulfinic acid [1-(8-cyclopropylmethyl-1,4-dioxa-spiro[4.5]dec-8-yl)-2,2,2-trifluoro-ethyl]-amideYield 79.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2-methyl-propane-2-sulfinic acid 1-(8-cyclopropylmethyl-1,4-dioxa-spiro[4.5]dec-8-yl)-methylideneamide (19, 1.00 g, 3.05 mmol) in tetrahydrofuran was cooled to −40° C. and was treated sequentially with tetramethylammonium fluoride (313 mg, 3.36 mmol, 1.1 eq.) and (trifluoromethyl)trimethylsilane (587 μL, 3.97 mmol, 1.3 eq.). The mixture was stirred for 2 h at 0° C. before being quenched by addition of saturated aqueous ammonium chloride solution and extracted twice with ethyl acetate. The combined organic layers were dried over magnesium sulphate, filtered, and concentrated in vacuo to give 960 mg of the title compound. Rt=1.63 min (Method B). Detected mass: 398.3 (M+H+).

Workup

  1. custombefore being quenched by addition of saturated aqueous ammonium chloride solution
  2. extractionextracted twice with ethyl acetate
  3. dry with materialThe combined organic layers were dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-78bdad02ff874d5e803ce2c84a803270
Source dataset
uspto-grants-2013_03
Patent number
US08399482B2

Reaction notes

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