Sodium cyanoborohydride → HCID 10377267, compound

HRID 1743866Notes

Reaction equation

HRID 1743866 reaction equation
[F: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>[F: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 10332074HCID 10332074, compound

Product 1

HCID 10377267HCID 10377267, compoundYield 84.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 8-fluoro-2,3,4,5,10,11-hexahydro-1H,9H-cyclopenta[b][1,4]diazocino[7,8,1-hi]indole (0.41 g, 1.68 mmole) in acetic acid (50 mL) was added sodium cyanoborohydride (0.33 g, 4.99 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 0.35 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 169-170° C. MS (ES) m/z 247.13 ([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-045dcdc438c84fecbde3e822a60e08b7
Source dataset
uspto-grants-2006_03
Patent number
US07012089B2

Reaction notes

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