Sodium cyanoborohydride → HCID 10244368, compound

HRID 1743867Notes

Reaction equation

HRID 1743867 reaction equation
[F:1][C:2]1[CH:14]=[CH:13][C:12]2[CH2:15][CH2:16][NH:17][CH2:18][CH2:19][N:10]3[C:11]=2[C:3]=1[C:4]1[CH2:5][CH2:6][CH2:7][CH2:8][C:9]=13.C([BH3-])#N.[Na+]>C(O)(=O)C>[F:1][C:2]1[CH:14]=[CH:13][C:12]2[CH2:15][CH2:16][NH:17][CH2:18][CH2:19][N:10]3[C:11]=2[C:3]=1[CH:4]1[CH:9]3[CH2:8][CH2:7][CH2:6][CH2:5]1

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 10220778HCID 10220778, compound

Product 1

HCID 10244368HCID 10244368, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 8-fluoro-2,3,4,5,9,10,11,12-octahydro-1H-[1,4]diazocino[7,8,1-jk]carbazole (0.30 g, 1.16 mmole) in acetic acid (50 mL) was added sodium cyanoborohydride (0.22 g, 3.32 mmole) and the reaction mixture was stirred at room temperature for 4 hours. 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 0.23 g of the title compound as a colorless oil. The oil was further treated with one equivalent of fumaric acid in ethanol to form a fumarate salt, mp 189-190° C. MS (ESI) m/z 261 ([M+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-c158754a7ed64f809ac4f4f35ac99953
Source dataset
uspto-grants-2006_03
Patent number
US07012089B2

Reaction notes

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