Aluminium lithium hydride → 7-fluoro-3,4-dihydro-1,5-benzothiazepin-5(2H)-amine

HRID 1764796노트

반응식

HRID 1764796 반응식
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[S:11][CH2:10][CH2:9][CH2:8][N:7]([N:12]=O)[C:6]=2[CH:14]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[S:11][CH2:10][CH2:9][CH2:8][N:7]([NH2:12])[C:6]=2[CH:14]=1

참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 220367967-Fluoro-5-nitroso-2,3,4,5-tetrahydro-1,5-benzothiazepine

생성물 1

HCID 220368027-fluoro-3,4-dihydro-1,5-benzothiazepin-5(2H)-amine수율 112.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

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.

후처리

  1. distillationof freshly distilled) and
  2. customThe flask was removed from the ice bath
  3. temperatureto warm to room temperature
  4. additionWater (0.08 mL) was added
  5. stirringstirred for 10 minutes
  6. addition15% sodium hydroxide (0.08 mL) was added
  7. stirringstirred for 10 minutes
  8. additionWater (0.024 mL) was added
  9. stirringstirred for 10 minutes
  10. extractionThe reaction was extracted with dichloromethane (2×25 mL)
  11. concentrationThe organics were concentrated to a residue
  12. additionhydrogen chloride in ether (1 M) was added until precipitation
  13. customformed
  14. filtrationthe precipitate was filtered off

출처 및 근거

ORD 기록
ord-fdef9e1507b040fe965a95c4435d5c07
출처 데이터셋
uspto-grants-2007_06
특허 번호
USRE039680E1

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