Acetic Acid → HCID 25265627, compound

HRID 2194831Notes

Reaction equation

HRID 2194831 reaction equation
[C:1]1([N:7]2[C:11]([CH:12]=O)=[CH:10][CH:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:14]1([C@H:24]([NH2:26])[CH3:25])[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1.C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl>[C:14]1([C@H:24]([NH:26][CH2:12][C:11]2[N:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[N:8]=[CH:9][CH:10]=2)[CH3:25])[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 2724264(+)-1-(1-Naphthyl)ethylamineHCID 27765671-phenyl-1H-pyrazole-5-carbaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 25265627HCID 25265627, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 1-phenyl-1H-pyrazole-5-carbaldehyde 38 (0.517 g, 3 mmol) in DCE (10 mL) at room temperature was added (R)-1-(naphthalen-1-yl)ethanamine 39 (0.625 g, 4 mmol), acetic acid (0.208 g, 3 mmol), and NaBH(OAc)3 (0.946 g, 4 mmol). The reaction mixture was stirred at room temperature for 18 h, quenched with saturated NaHCO3, diluted with EtOAc, washed with saturated NaHCO3 (1×), brine (1×), dried over MgSO4, filtered, and concentrated. Purification by flash column chromatography on silica gel (eluted with 20% to 70% EtOAc in hexanes) gave (1R)-1-(1-naphthalenyl)-N-((1-phenyl-1H-pyrazol-5-yl)methyl)ethanamine 40. Mass spectrum: calculated for C22H21N3 327.2; found 328.2 (M++1).

Workup

  1. customquenched with saturated NaHCO3
  2. additiondiluted with EtOAc
  3. washwashed with saturated NaHCO3 (1×), brine (1×)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash column chromatography on silica gel (eluted with 20% to 70% EtOAc in hexanes)

Sources & evidence

ORD record
ord-0ff2a0a736ee4566a011d1827991d80f
Source dataset
uspto-grants-2012_12
Patent number
US08334317B2

Reaction notes

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