Tetrahydro-beta-carboline → HCID 21873849, 화합물

HRID 406511

반응식

HRID 406511 반응식
[CH2:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH2:4][CH2:3][NH:2]1.C([BH3-])#N.[Na+]>C(O)(C(F)(F)F)=O>[CH2:1]1[CH:13]2[CH:5]([C:6]3[C:11]([NH:12]2)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH2:4][CH2:3][NH:2]1

참가 물질

4

반응물 2

HCID 107838Tetrahydro-beta-carbolineHCID 5003444Sodium cyanoborohydride

생성물 1

HCID 21873849HCID 21873849, 화합물수율 72.3%

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

실험 절차

To a solution of 2,3,4,9-tetrahydro-1H-beta-carboline (0.100 g, 0.581 mmol) in TFA (1 mL) was added sodium cyanoborohydride (0.109 g, 1.74 mmol) and the reaction mixture was stirred at ambient temperature for about 16 h. The reaction mixture was concentrated in vacuo and the residue was partitioned between water (25 mL) and dichloromethane (50 mL). The organic layer was separated and the aqueous layer was further extracted with dichloromethane (2×50 mL). The combined organic extracts were dried over magnesium sulfate, and evaporated under reduced pressure. The residue was purified by using preparative RP-HPLC (Rainin C18, 8 mm, 300 Å, 35 cm; 5-100% acetonitrile—0.1M ammonium acetate over 20 min, 100% acetonitrile hold 10 minutes, 21 mL/min) to give 2,3,4,4a,9,9a-hexahydro-1H-beta-carboline (0.073 g, 0.42 mmol) as a brown oil; RP-HPLC (Table 1, Method a) Rt 1.35 min; m/z: (M+H)+ 175.

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was partitioned between water (25 mL) and dichloromethane (50 mL)
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was further extracted with dichloromethane (2×50 mL)
  5. dry with materialThe combined organic extracts were dried over magnesium sulfate
  6. customevaporated under reduced pressure
  7. customThe residue was purified
  8. customRP-HPLC (Rainin C18, 8 mm, 300 Å, 35 cm; 5-100% acetonitrile—0.1M ammonium acetate over 20 min, 100% acetonitrile hold 10 minutes, 21 mL/min)

출처 및 근거

ORD 기록
ord-c345b77ed67e450e9519b37c47363791
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08754107B2

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