Sodium cyanoborohydride → HCID 86605388, compound

HRID 1180423Notes

Reaction equation

HRID 1180423 reaction equation
[I-].[CH3:2][O:3][C:4]([C@@H:6]([O:11][C@H:12]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:20]=[N+:21]([CH3:25])[CH:22]=[CH:23][CH:24]=2)=[CH:15][CH:14]=1)[CH2:7][CH:8]([CH3:10])[CH3:9])=[O:5].C([BH3-])#N.[Na+]>CO>[CH3:9][CH:8]([CH3:10])[CH2:7][C@H:6]([O:11][C@@H:12]([C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH2:20][N:21]([CH3:25])[CH2:22][CH2:23][CH:24]=2)=[CH:15][CH:14]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:4]([O:3][CH3:2])=[O:5]

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 69473245HCID 69473245, compound

Product 1

HCID 86605388HCID 86605388, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 3-{4-[(R)-{[(1S)-1-(methoxycarbonyl)-3-methylbutyl]oxy}(phenyl)methyl]phenyl}-1-methylpyridinium iodide from example 36 step 3 (1.45 g, 2.72 mmol) in methanol (25 mL) was added in portions sodium cyanoborohydride (4.25 g, 67.6 mmol). The mixture was heated at 65° C. for 1 h and then concentrated. The residue was partitioned between diethyl ether (75 mL) and water (25 mL). The separated aqueous layer was extracted again with diethyl ether (75 mL). The combined ether layers were dried (Na2SO4), filtered, concentrated and chromatographed on silica gel using 10% methanol in dichloromethane as eluent to obtain the title compound as an oil.

Workup

  1. concentrationconcentrated
  2. customThe residue was partitioned between diethyl ether (75 mL) and water (25 mL)
  3. extractionThe separated aqueous layer was extracted again with diethyl ether (75 mL)
  4. dry with materialThe combined ether layers were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customchromatographed on silica gel using 10% methanol in dichloromethane as eluent

Sources & evidence

ORD record
ord-1e4225725e9245cc9bcf6df561c84673
Source dataset
uspto-grants-2007_10
Patent number
US07279478B2

Reaction notes

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