4-Formylbenzoic acid → HCID 86708253, compound

HRID 529355Notes

Reaction equation

HRID 529355 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]([N:5]([C@H:13]1[CH2:15][C@@H:14]1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:6][CH:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1)=[O:4].[CH:24]([C:26]1[CH:34]=[CH:33][C:29]([C:30]([OH:32])=[O:31])=[CH:28][CH:27]=1)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[F:23][C:2]([F:1])([F:22])[C:3]([N:5]([CH2:6][CH:7]1[CH2:8][CH2:9][N:10]([CH2:24][C:26]2[CH:34]=[CH:33][C:29]([C:30]([OH:32])=[O:31])=[CH:28][CH:27]=2)[CH2:11][CH2:12]1)[C@@H:13]1[CH2:15][C@H:14]1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:4]

Participants

5

Reactant 3

HCID 120884-Formylbenzoic acidHCID 5049666Sodium triacetoxyborohydrideHCID 86708254HCID 86708254, compound

Product 1

HCID 86708253HCID 86708253, compoundYield 52.5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 2,2,2-trifluoro-N-((1S,2R)-2-phenylcyclopropyl)-N-(piperidin-4-ylmethyl)acetamide (243 mg, 0.745 mmol) in 1,2-dichloroethane (DCE) (4 mL) were added 4-formylbenzoic acid (134 mg, 0.894 mmol) and sodium triacetoxyborohydride (252 mg, 1.191 mmol), and the mixture was stirred at room temperature for 18 h. The reaction was quenched with water (4 mL) and extracted with CH2Cl2 (3×). The extract was dried (Na2SO4) and concentrated. The residue was purified using column chromatography (silica gel, 0 to 5% MeOH/EtOAc) to give 180 mg of product as pale yellow solid. MS: (M+H)+=461.3. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.12-1.32 (m, 2H), 1.35-1.47 (m, 1H), 1.53-1.82 (m, 3H), 1.88-2.05 (m, 2H), 2.81 (br. s., 2H), 3.09-3.22 (m, 2H), 3.26-3.41 (m, 2H), 3.27-3.43 (m, 2H), 7.09-7.35 (m, 5H), 7.39-7.50 (m, 2H), 7.86-7.94 (m, 2H).

Workup

  1. customThe reaction was quenched with water (4 mL)
  2. extractionextracted with CH2Cl2 (3×)
  3. dry with materialThe extract was dried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was purified

Sources & evidence

ORD record
ord-60a8c90ab18d446a8ef84a49b1044e38
Source dataset
uspto-grants-2016_05
Patent number
US09346840B2

Reaction notes

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