Sodium Bicarbonate → HCID 59178549, compound

HRID 1691675Notes

Reaction equation

HRID 1691675 reaction equation
[C:1]1([C@H:11]([NH2:13])[CH3:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[C:28]1([C@H:34]2[CH2:39][CH2:38][N:37]([C:40](=[O:45])[C:41]([F:44])([F:43])[F:42])[CH2:36][C@@H:35]2[CH:46]=O)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(=O)([O-])O.[Na+]>ClCCCl.C(O)(=O)C>[C:1]1([C@H:11]([NH:13][CH2:46][CH:35]2[CH:34]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:39][CH2:38][N:37]([C:40](=[O:45])[C:41]([F:44])([F:42])[F:43])[CH2:36]2)[CH3:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 2724264(+)-1-(1-Naphthyl)ethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 86638695HCID 86638695, compound

Product 1

HCID 59178549HCID 59178549, compoundYield 82.4%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolvent2×HCID 176Acetic AcidSolvent

Procedure

To a mixture of 868 mg of (1R)-1-(1-naphthyl)ethaneamine, 0.073 mL of acetic acid, 1.29 g of sodium triacetoxyborohydride, and 75 mL of 1,2-dichloroethane was added dropwise a solution of 1.446 g of a crude rel-(3R,4S)-4-phenyl-1-(trifluoroacetyl)piperidine-3-carbaldehyde in 25 mL of 1,2-dichloroethane at room temperature, followed by stirring overnight. To the reaction mixture was added a saturated aqueous sodium hydrogen carbonate solution, followed by vigorously stirring for 10 minutes, and then extracting with chloroform, and the organic layer was dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform-methanol) to obtain 1.84 g of (1R)-1-(1-naphthyl)-N-{[4-phenyl-1-(trifluoroacetyl)piperidin-3-yl]methyl}ethaneamine as a colorless foamy substance.

Workup

  1. stirringby vigorously stirring for 10 minutes
  2. extractionextracting with chloroform
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-39cddd5b323f4bb1906f86823a1dc0a0
Source dataset
uspto-grants-2012_04
Patent number
US08153658B2

Reaction notes

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