Sodium Bicarbonate → HCID 86649011, compound

HRID 1877874Notes

Reaction equation

HRID 1877874 reaction equation
[Cl:1][C:2]1[C:3]([CH:16]=O)=[N:4][CH:5]=[C:6]([N:8]2[CH2:12][CH2:11][CH2:10][CH:9]2[CH2:13][O:14][CH3:15])[N:7]=1.[CH2:18]([NH:25][CH2:26][C@@H:27]([OH:31])[CH2:28][O:29][CH3:30])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(#N)C.C(O)(=O)C>[CH2:18]([N:25]([CH2:16][C:3]1[C:2]([Cl:1])=[N:7][C:6]([N:8]2[CH2:12][CH2:11][CH2:10][CH:9]2[CH2:13][O:14][CH3:15])=[CH:5][N:4]=1)[CH2:26][C@@H:27]([OH:31])[CH2:28][O:29][CH3:30])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 34179216HCID 34179216, compoundHCID 866490103-Chloro-5-[2-(methoxymethyl)pyrrolidin-1-yl]pyrazine-2-carbaldehyde

Product 1

HCID 86649011HCID 86649011, compoundYield 67.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-chloro-5-[2-(methoxymethyl)pyrrolidin-1-yl]pyrazine-2-carbaldehyde (511 mg), (2R)-1-(benzylamino)-3-methoxypropan-2-ol (469 mg) and acetic acid (343 μL) in acetonitrile (10 mL) was added sodium triacetoxyborohydride (636 mg), and the mixture was stirred at room temperature for 14.5 hr. To the reaction mixture was added dropwise a saturated sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (solvent gradient: 10→50% ethyl acetate/hexane) to give the title compound (583 mg, 67%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (solvent gradient: 10→50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-9f180a985db64f86aee200c71ce7c2ee
Source dataset
uspto-grants-2012_11
Patent number
US08314088B2

Reaction notes

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