Acetic Acid → HCID 178445678, compound

HRID 561357Notes

Reaction equation

HRID 561357 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH:8]=O)[CH:5]=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([NH2:18])=[O:17])[CH:11]=1.[C:19]([CH:23]1[CH2:28][CH2:27][CH:26]([NH2:29])[CH2:25][CH2:24]1)([CH3:22])([CH3:21])[CH3:20].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.CCOC(C)=O>[C:19]([C@@H:23]1[CH2:24][CH2:25][C@H:26]([NH:29][CH2:8][C:6]2[CH:5]=[CH:4][C:3]([C:10]3[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([NH2:18])=[O:17])[CH:11]=3)=[C:2]([F:1])[CH:7]=2)[CH2:27][CH2:28]1)([CH3:22])([CH3:20])[CH3:21]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 793964-tert-ButylcyclohexylamineHCID 5049666Sodium triacetoxyborohydrideHCID 593163992'-Fluoro-4'-formylbiphenyl-3-carboxylic acid amide

Product 1

HCID 178445678HCID 178445678, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 2′-fluoro-4′-formylbiphenyl-3-carboxylic acid amide (Preparation 9, 252 mg, 1.0 mmol) in DCM (100 mL) was added 4-tert-butylcyclohexylamine (500 μL, 3.2 mmol), acetic acid (200 μL, 3.5 mmol) and sodium triacetoxyborohydride (648 mg, 3.1 mmol). The mixture was stirred at rt for 16 h. EtOAc (100 mL) was added and the organics washed with aqueous NaHCO3 (30 mL), brine (30 mL) and dried (MgSO4). The solvent was removed in vacuo and the residue purified by column chromatography (17% EtOH: Toluene) to give cis-4′-[(4-tert-butylcyclohexylamino)methyl]-2′-fluorobiphenyl-3-carboxylic acid amide: RT=2.84 min; m/z (ES+)=383.0 [M+H]+, and trans-4′-[(4-tert-butylcyclohexylamino)methyl]-2′-fluorobiphenyl-3-carboxylic acid amide: RT=2.87 min; m/z (ES+)=383.0 [M+H]+.

Workup

  1. washthe organics washed with aqueous NaHCO3 (30 mL), brine (30 mL)
  2. dry with materialdried (MgSO4)
  3. customThe solvent was removed in vacuo
  4. customthe residue purified by column chromatography (17% EtOH: Toluene)

Sources & evidence

ORD record
ord-050f5f8a0a92457a8ad4c9c72f219202
Source dataset
uspto-grants-2011_11
Patent number
US08063247B2

Reaction notes

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