反应 #1851978

反应方程式

7-fluoro-5-nitroso-2,3,4,5-tetrahydro-1,5-benzothiazepine

Lithium aluminum hydride

→

7-fluoro-3,4-dihydro-1,5-benzothiazepin-5(2H)-amine

收率 112.6%

溶剂

THF

反应条件

后处理

1. 1
   workup.DISTILLATIONof freshly distilled) and
2. 2
   其他The flask was removed from the ice bath
3. 3
   温度to warm to room temperature
4. 4
   workup.ADDITIONWater (0.08 mL) was added
5. 5
   workup.STIRRINGstirred for 10 minutes
6. 6
   workup.ADDITION15% sodium hydroxide (0.08 mL) was added
7. 7
   workup.STIRRINGstirred for 10 minutes
8. 8
   workup.ADDITIONWater (0.024 mL) was added
9. 9
   workup.STIRRINGstirred for 10 minutes
10. 10
    萃取The reaction was extracted with dichloromethane (2×25 mL)
11. 11
    浓缩The organics were concentrated to a residue
12. 12
    workup.ADDITIONhydrogen chloride in ether (1 M) was added until precipitation
13. 13
    其他formed
14. 14
    过滤the precipitate was filtered off

实验过程

7-fluoro-5-nitroso-2,3,4,5-tetrahydro-1,5-benzothiazepine (449 mg, 2.11 mmol) was suspended in THF (1 mL of freshly distilled) and cooled to 0° C. in an ice bath. Lithium aluminum hydride (80 mg, 2.11 mmol) was added in a portion-wise fashion. The flask was removed from the ice bath and allowed to warm to room temperature and was stirred for 2 hours. Water (0.08 mL) was added and stirred for 10 minutes. 15% sodium hydroxide (0.08 mL) was added stirred for 10 minutes. Water (0.024 mL) was added and stirred for 10 minutes. The reaction was extracted with dichloromethane (2×25 mL). The organics were concentrated to a residue, then taken up in minimal amount of dichloromethane and then hydrogen chloride in ether (1 M) was added until precipitation formed, the precipitate was filtered off to give 7-fluoro-3,4-dihydro-1,5-benzothiazepin-5(2H)-amine (471 mg, 95%). 1H NMR (CD3OD, 300 MHz): δ 7.59 (t, 1H, J=7.5 Hz), 7.28 (d, 1H, J=9.9 Hz), 7.00 (t, 1H, J=8.2 Hz), 3.52 (t, 1H, J=7.5 Hz), 2.92-2.86 (m, 1H), 2.72-2.70 (m, 2H), 2.40-2.31 (m, 1H), 2.2-2.18 (m, 2H) ppm.

来源