Tetrahydrofuran → HCID 178440768, compound

HRID 2242255Notes

Reaction equation

HRID 2242255 reaction equation
[CH2:1]([N:3](CC)CC)C.[CH2:8]1[CH2:12]OC[CH2:9]1.[CH2:13]([C:17]1[CH:22]=[CH:21][C:20]([C:23]2[O:27][N:26]=[C:25]([C:28]3[CH:35]=[CH:34][C:31](C=O)=[CH:30][CH:29]=3)[N:24]=2)=[CH:19][CH:18]=1)[CH:14]([CH3:16])[CH3:15].C(O[BH-]([O:45][C:46](=[O:48])[CH3:47])OC(=O)C)(=O)C.[Na+].[C:50](O)(=O)C.[CH2:54]1[CH2:58]OC[CH2:55]1>CO>[C:54]([O:45][C:46]([C@H:47]1[CH2:12][C@@H:8]([NH:3][CH2:1][C:31]2[CH:34]=[CH:35][C:28]([C:25]3[N:24]=[C:23]([C:20]4[CH:19]=[CH:18][C:17]([CH2:13][CH:14]([CH3:15])[CH3:16])=[CH:22][CH:21]=4)[O:27][N:26]=3)=[CH:29][CH:30]=2)[CH2:9]1)=[O:48])([CH3:55])([CH3:58])[CH3:50]

Participants

7

Reactant 5

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 184469664-[5-[4-(2-Methylpropyl)phenyl]-1,2,4-oxadiazol-3-YL]benzaldehydeHCID 23444217Acetic acid tetrahydrofuran

Product 1

HCID 178440768HCID 178440768, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-cis-amino-cylcobutanecarboxylic acid tert-butyl ester (3.78 g, 19.6 mmol), triethylamine (4.0 mL, 29.4 mmol) and THF (100 mL) was added to a solution of 4-[5-(4-isobutyl-phenyl)-[1,2,4]oxadiazol-3-yl]-benzaldehyde (6.0 g, 19.6 mmol) in acetic acid/THF (1:10, 100 mL) and stirred at room temperature for 1 hour. Sodium triacetoxyborohydride (8.06 g, 39.2 mmol) was added to the reaction mixture, stirred at room temperature for 12 hours, treated with methanol (50.0 mL) and concentrated in vacuo. The resulting residue was taken up in dichloromethane, washed sequentially with brine, saturated NaHCO3 and brine, dried (Na2SO4), filtered and concentrated in vacuo. Purification by flash chromatography (silica, 1:9-1:1 EtOAc:hexanes) provided the title compound (4.0 g, 44% yield) as a solid.

Workup

  1. stirringstirred at room temperature for 12 hours
  2. concentrationconcentrated in vacuo
  3. washwashed sequentially with brine, saturated NaHCO3 and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by flash chromatography (silica, 1:9-1:1 EtOAc:hexanes)

Sources & evidence

ORD record
ord-6d136bed5041475caa5d756bb0b224bd
Source dataset
uspto-grants-2010_03
Patent number
US07671043B2

Reaction notes

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