Sodium cyanoborohydride → HCID 10354397, compound

HRID 1743830Notes

Reaction equation

HRID 1743830 reaction equation
[CH3:1][N:2]1[CH2:15][CH2:14][C:12]2=[C:13]3[C:8](=[CH:9][CH:10]=[CH:11]2)[C:7]2[CH2:16][CH2:17][CH2:18][C:6]=2[N:5]3[CH2:4][CH2:3]1.C([BH3-])#N.[Na+]>C(O)(=O)C>[CH3:1][N:2]1[CH2:15][CH2:14][C:12]2=[C:13]3[C:8](=[CH:9][CH:10]=[CH:11]2)[CH:7]2[CH2:16][CH2:17][CH2:18][CH:6]2[N:5]3[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 10263687HCID 10263687, compound

Product 1

HCID 10354397HCID 10354397, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 3-methyl-2,3,4,5,10,11-hexahydro-1H,9H-cyclopenta[b][1,4]diazocino[7,8,1-hi]indole (0.40 g, 1.7 mmole) in acetic acid (50 mL) was added sodium cyanoborohydride (95 wt. %, 0.21 g, 3.2 mmole) and the reaction mixture was stirred at room temperature for 1 hour. The solvent was removed in vacuo and the residue was diluted with ethyl acetate (300 mL) and washed with saturated aqueous sodium bicarbonate (150 mL) and saturated aqueous sodium chloride (150 mL), dried (sodium sulfate) and concentrated in vacuo. Purification by flash column chromatography (silica gel, ethyl acetate:hexanes 3:2) provided 0.40 g of the title compound as a light oil. 60 mg of this oil was treated with one equivalent of fumaric acid in ethanol to form a fumarate salt, mp 159-161° C. MS (ESI) m/z 243 ([M+H]+).

Workup

  1. customThe solvent was removed in vacuo
  2. additionthe residue was diluted with ethyl acetate (300 mL)
  3. washwashed with saturated aqueous sodium bicarbonate (150 mL) and saturated aqueous sodium chloride (150 mL)
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated in vacuo
  6. customPurification by flash column chromatography (silica gel, ethyl acetate:hexanes 3:2)

Sources & evidence

ORD record
ord-743d39bb4bbe4ee8bec6824321d3bf17
Source dataset
uspto-grants-2006_03
Patent number
US07012089B2

Reaction notes

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