Sodium borohydride → Ethyl 1-(2-Aminoethyl)-6,6-difluoro-4,5,6,7-tetrahydro-1H-indole-2-carboxylate

HRID 519330노트

반응식

HRID 519330 반응식
[C:1]([CH2:3][N:4]1[C:12]2[CH2:11][C:10]([F:14])([F:13])[CH2:9][CH2:8][C:7]=2[CH:6]=[C:5]1[C:15]([O:17][CH2:18][CH3:19])=[O:16])#[N:2].[BH4-].[Na+]>C(O)C>[NH2:2][CH2:1][CH2:3][N:4]1[C:12]2[CH2:11][C:10]([F:14])([F:13])[CH2:9][CH2:8][C:7]=2[CH:6]=[C:5]1[C:15]([O:17][CH2:18][CH3:19])=[O:16]

참가 물질

4

반응물 2

HCID 4311764Sodium borohydrideHCID 86683734Ethyl 1-(Cyanomethyl)-6,6-difluoro-4,5,6,7-tetrahydro-1H-indole-2-carboxylate

생성물 1

HCID 86683733Ethyl 1-(2-Aminoethyl)-6,6-difluoro-4,5,6,7-tetrahydro-1H-indole-2-carboxylate수율 21%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

Into a 100-mL round-bottom flask was placed a solution of 113m (3.3 g, 12.30 mmol, 1.00 equiv) in ethanol (30 mL) and NiCl2.6H2O (3.2 g, 13.45 mmol, 1.10 equiv), followed by the addition of NaBH4 (1.4 g, 37.01 mmol, 3.00 equiv) in several batches at 0° C. (FIG. 14). The resulting solution was stirred at room temperature for 24 h. The solids were filtered out and the filtrate was concentrated under vacuum. The resulting solution was diluted with 30 mL of ethyl acetate and washed with 1×30 mL of hydrogen chloride (2 N). The solution was adjusted to pH=9 with saturated aqueous sodium bicarbonate and extracted with 2×30 mL of ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated under vacuum to afford 0.7 g (21%) of 113n as a light yellow oil.

후처리

  1. customInto a 100-mL round-bottom flask was placed
  2. filtrationThe solids were filtered out
  3. concentrationthe filtrate was concentrated under vacuum
  4. additionThe resulting solution was diluted with 30 mL of ethyl acetate
  5. washwashed with 1×30 mL of hydrogen chloride (2 N)
  6. extractionextracted with 2×30 mL of ethyl acetate
  7. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  8. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-484af358661445aa8501b87a1c3f87b1
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09115152B2

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