Sodium cyanoborohydride → HCID 10422838, compound

HRID 1743881Notes

Reaction equation

HRID 1743881 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[CH2:11][CH2:12][NH:13][CH2:14][CH2:15][N:6]3[C:7]=2[C:3]=1[C:4]1[CH2:18][CH2:17][CH2:16][C:5]=13.C([BH3-])#N.[Na+]>C(O)(=O)C>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[CH2:11][CH2:12][NH:13][CH2:14][CH2:15][N:6]3[C:7]=2[C:3]=1[CH:4]1[CH2:18][CH2:17][CH2:16][CH:5]13

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 10244387HCID 10244387, compound

Product 1

HCID 10422838HCID 10422838, compoundYield 49.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 8-chloro-2,3,4,5,10,11-hexahydro-1H,9H-cyclopenta[b][1,4]diazocino[7,8,1-hi]indole (0.60 g, 2.30 mmole) in acetic acid (100 mL) was added sodium cyanoborohydride (0.60 g, 9.07 mmole) and the reaction mixture was stirred at room temperature overnight. The solvent was removed in vacuo and the residue was diluted with methylene chloride (200 mL) and washed with aqueous sodium hydroxide (1N, 150 mL), saturated sodium chloride (150 mL), dried (sodium sulfate) and concentrated. Purification by flash column chromatography (silica gel, 1.5% to 5% methanol in methylene chloride) provided 0.30 g of the title compound as a white solid. 60 mg of this compound was further treated with one equivalent of fumaric acid in ethanol to form a fumarate salt, mp 169-170° C. MS (ES) m/z 263.1 ([M+H]+), MS (ES) m/z 304.1 ([M+ACN+H]+).

Workup

  1. customThe solvent was removed in vacuo
  2. additionthe residue was diluted with methylene chloride (200 mL)
  3. washwashed with aqueous sodium hydroxide (1N, 150 mL), saturated sodium chloride (150 mL)
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated
  6. customPurification by flash column chromatography (silica gel, 1.5% to 5% methanol in methylene chloride)

Sources & evidence

ORD record
ord-43558da913974df6820c16ca08ab33e4
Source dataset
uspto-grants-2006_03
Patent number
US07012089B2

Reaction notes

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