Tetrahydro-beta-carboline → HCID 21873849, compound

HRID 406511

Reaction equation

HRID 406511 reaction equation
[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

Participants

4

Reactant 2

HCID 107838Tetrahydro-beta-carbolineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 21873849HCID 21873849, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-c345b77ed67e450e9519b37c47363791
Source dataset
uspto-grants-2014_06
Patent number
US08754107B2

Linked notes

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