Reaktion #73478

Reaktionsgleichung

9-BBN

2-methyl-propane-2-sulfinic acid {1-[8-(4-fluoro-phenyl)-1,4-dioxa-spiro[4.5]dec-8-yl]allyl}-amide

2-Methyl-propane-2-sulfinic acid {1-[8-(4-fluoro-phenyl)-1,4-dioxa-spiro[4.5]dec-8-yl]-allyl}-amide

iodomethane

sodium hydride

ammonium hydroxide

sodium hydride

sodium hydroxide

hydrogen peroxide

→

title compound ( 107 )

2-Methyl-propane-2-sulfinic acid {1-[8-(4-fluoro-phenyl)-1,4-dioxa-spiro[4.5]dec-8-yl]-3-methoxy-propyl}-amide

Lösungsmittel

tetrahydrofuran

THF

methanol

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturbefore being cooled to 0° C
2. 2
   ExtraktionThe mixture was extracted twice with 50 mL of ethyl acetate
3. 3
   Waschenwashed with water and saturated sodium chloride solution
4. 4
   Trocknendried over magnesium sulfate
5. 5
   Einengenconcentrated in vacuo
6. 6
   workup.DISSOLUTIONThe crude alcohol was dissolved in 5 mL of tetrahydrofuran
7. 7
   workup.ADDITIONwere added
8. 8
   workup.STIRRINGThe reaction mixture was stirred for 1 h at room temperature
9. 9
   SonstigeThe reaction mixture was evaporated to dryness

Vorschrift

16.5 mL (8.23 mmol) of a 0.5M solution of 9-BBN in tetrahydrofuran were added to a solution of 1.09 g (2.74 mmol) of 2-methyl-propane-2-sulfinic acid {1-[8-(4-fluoro-phenyl)-1,4-dioxa-spiro[4.5]dec-8-yl]allyl}-amide (106) in 5 mL THF at 0° C. The reaction mixture was allowed to warm to room temperature over night, before being cooled to 0° C. Then, 20 mL of 3M aqueous sodium hydroxide and 7.5 mL of 30% aqueous hydrogen peroxide were added slowly, and the mixture was stirred for 16 h at room temperature. The mixture was extracted twice with 50 mL of ethyl acetate, washed with water and saturated sodium chloride solution, dried over magnesium sulfate and concentrated in vacuo. The crude alcohol was dissolved in 5 mL of tetrahydrofuran and added slowly to a suspension of 131 mg (4.46 mmol) of sodium hydride (60%) in 5 mL tetrahydrofuran at 0° C. 515 μL (8.20 mmol) of iodomethane were added, and after stirring for 16 h at room temperature another 50 mg of sodium hydride (60%) were added. The reaction mixture was stirred for 1 h at room temperature, then 30 mL of methanol and 15 mL of aqueous ammonium hydroxide solution (33%) were added. The reaction mixture was evaporated to dryness and lyophilized from water to give 1.17 g of the title compound (107) in a purity sufficient for further conversion. Rt=0.93 min (Method 18). Detected mass: 428.2 (M+H+).

Quelle