Acetic Acid → HCID 59803184, compound

HRID 1801593Notes

Reaction equation

HRID 1801593 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=O)=[CH:4][C:3]=1[N:10]1[CH2:15][CH2:14][CH:13]([C:16]([O:18][CH3:19])=[O:17])[CH2:12][CH2:11]1.[C:20]1([C@H:26]([NH2:28])[CH3:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:28][C@@H:26]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH3:27])=[CH:4][C:3]=1[N:10]1[CH2:15][CH2:14][CH:13]([C:16]([O:18][CH3:19])=[O:17])[CH2:12][CH2:11]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6431891-Phenethylamine, (+)-HCID 5049666Sodium triacetoxyborohydrideHCID 59803209HCID 59803209, compound

Product 1

HCID 59803184HCID 59803184, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of methyl 1-(2-chloro-5-formylphenyl)piperidine-4-carboxylate 68 (0.180 g, 0.64 mmol) in DCE (3 mL) was added (R)-1-phenylethanamine (0.10 mL, 0.79 mmol), acetic acid (0.040 mL, 0.69 mmol), and NaBH(OAc)3 (0.168 g, 0.79 mmol). The reaction mixture was stirred at room temperature for 20 h, quenched with saturated NaHCO3, and diluted with EtOAc. The organic phase was washed with saturated NaHCO3 (1×), brine (1 x), dried over MgSO4, filtered, and concentrated in vacuo. Purification by flash column chromatography on silica gel (eluted with 50% to 100% EtOAc in hexanes) gave (R)-methyl 1-(2-chloro-5-((1-phenylethylamino)methyl)phenyl)piperidine-4-carboxylate 69 (0.215 g, 87% yield) as a colorless oil. Mass spectrum: calculated for C22H27ClN2O2 386.2. found 387.2 (M++1).

Workup

  1. customquenched with saturated NaHCO3
  2. additiondiluted with EtOAc
  3. washThe organic phase was washed with saturated NaHCO3 (1×), brine (1 x)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by flash column chromatography on silica gel (eluted with 50% to 100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-4089d966d74c403ca05c1ceb08f28159
Source dataset
uspto-grants-2013_01
Patent number
US08349831B2

Reaction notes

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