Triethylamine → 8-(5-Fluoro-2-methylphenylsulfonyl)-1,4-dioxa-8-azaspiro[4.5]decane

HRID 597833Notes

Reaction equation

HRID 597833 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][NH:8][CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.CCN(CC)CC.[F:18][C:19]1[CH:20]=[CH:21][C:22]([CH3:29])=[C:23]([S:25](Cl)(=[O:27])=[O:26])[CH:24]=1>C1COCC1>[F:18][C:19]1[CH:20]=[CH:21][C:22]([CH3:29])=[C:23]([S:25]([N:8]2[CH2:9][CH2:10][C:5]3([O:4][CH2:3][CH2:2][O:1]3)[CH2:6][CH2:7]2)(=[O:27])=[O:26])[CH:24]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 1362865-Fluoro-2-methylbenzenesulphonyl chloride

Product 1

HCID 38146088-(5-Fluoro-2-methylphenylsulfonyl)-1,4-dioxa-8-azaspiro[4.5]decaneYield 100.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 1,4-dioxa-8-azaspiro[4,5]decane (10.73 g, 75 mmol) and Et3N (8 mL, 57 mmol) in THF (150 mL) was cooled in an ice-water bath. To this mixture was slowly added 5-fluoro-2-methylbenzenesulfonyl chloride (10.5 g, 50.33 mmol) and stirred for 1 h and then cold bath was removed. After 15 h at room temperature, the reaction mixture was diluted with ether (200 mL), washed with 1N aq. HCl (2×50 mL), brine (50 mL), dried (Na2SO4), filtered and concentrated to give product as an off-white solid 15.9 g, 100%). 1H NMR (500 MHz, CDCl3) δ: 7.61 (1H, dd, J=8.6, 2.8 Hz), 7.28-7.26 (1H, m), 7.15 (1H, td, J=8.1, 2.8 Hz), 3.94 (4H, s), 3.35-3.32 (4H, m), 2.57 (3H, s), 1.78-1.76 (4H, m). HRMS (M+H) calcd for C14H19FNO4S: 316.1019; found: 316.1013.

Workup

  1. customcold bath was removed
  2. waitAfter 15 h at room temperature
  3. additionthe reaction mixture was diluted with ether (200 mL)
  4. washwashed with 1N aq. HCl (2×50 mL), brine (50 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e5c64cb1b0074190b3bfe3616d9261b0
Source dataset
uspto-grants-2011_03
Patent number
US07897593B2

Reaction notes

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