反応 #165710

反応方程式

Iodine

8-oxabicyclo[3.2.1]octan-2-one

(R)-(tetrahydrofuran-2-yl)methanamine

potassium thiocyanate

→

crude material

収率 90.5%

3-[(2R)-tetrahydrofuran-2-ylmethyl]-3,4,5,6,7,8-hexahydro-2H-4,7-epoxycyclohepta[d][1,3]thiazol-2-imine

収率 90.5%

溶媒

acetonitrile

反応条件

後処理

1. 1
   ろ過The material was filtered through Celite® with acetonitrile (additional 10 mL)
2. 2
   workup.ADDITIONwas added
3. 3
   温度the mixture was warmed to 50° C
4. 4
   workup.STIRRINGthe mixture stirred at 50° C. for 72 h
5. 5
   温度The mixture was cooled to ambient temperature
6. 6
   濃縮was concentrated under reduced pressure
7. 7
   workup.ADDITIONThe crude material was diluted with 20 mL CH2Cl2
8. 8
   workup.STIRRINGwas stirred with sodium metabisulfite (20 mL of 20% aqueous solution) for 15 min
9. 9
   その他The layers were separated
10. 10
    抽出the aqueous layer was extracted 3×10 mL CH2Cl2
11. 11
    乾燥The combined organics were dried over Na2SO4
12. 12
    ろ過filtered
13. 13
    濃縮concentrated under reduced pressure

実験手順

A mixture of 8-oxabicyclo[3.2.1]octan-2-one (obtained as described in Vogel et al. Tetrahedron 1993, 49 (8), 1649-1664) (0.53 g, 4.2 mmol), (R)-(tetrahydrofuran-2-yl)methanamine (0.43 mL, 4.2 mmol) and 1 g of 4 Å molecular sieves (8-12 mesh beads) in acetonitrile (4 mL) was stirred at ambient temperature for 16 h. The material was filtered through Celite® with acetonitrile (additional 10 mL) then the filtrate treated with potassium thiocyanate (0.54 g, 5.6 mmol) was added and the mixture was warmed to 50° C. Iodine (2.1 g, 8.4 mmol) was added and the mixture stirred at 50° C. for 72 h. The mixture was cooled to ambient temperature and was concentrated under reduced pressure. The crude material was diluted with 20 mL CH2Cl2 and was stirred with sodium metabisulfite (20 mL of 20% aqueous solution) for 15 min. The layers were separated and the aqueous layer was extracted 3×10 mL CH2Cl2. The combined organics were dried over Na2SO4, filtered and concentrated under reduced pressure to give the crude material (1.0 g, 3.8 mmol, 89% yield) which was carried on without further purification. MS (DCI/NH3) m/z 267 (M+H)+.

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