Sodium Chloride → HCID 69317052, compound

HRID 2114840Notes

Reaction equation

HRID 2114840 reaction equation
[CH:1]([C:3]1([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:7][CH2:6][CH2:5][CH2:4]1)=O.[O:16]([C:18]1[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[CH:22][C:19]=1[CH2:20][NH2:21])[CH3:17].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+].[Na+].[Cl-]>C1COCC1.CCOC(C)=O>[CH3:17][O:16][C:18]1[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[CH:22][C:19]=1[CH2:20][NH:21][CH2:1][C:3]1([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

8

Reactant 5

HCID 5234Sodium ChlorideHCID 516892Sodium BicarbonateHCID 5972502,4-DimethoxybenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 16217741tert-Butyl (1-formylcyclopentyl)carbamate

Product 1

HCID 69317052HCID 69317052, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl 1-formylcyclopentylcarbamate (1.87 g, 8.78 mmol) in anhydrous THF (9 mL) was added 2,4-dimethoxylbenzylamine (1.98 mL, 13.17 mmol). The reaction was stirred for 10 min, treated with sodium triacetoxyborohydride (2.98 g, 14.04 mmol), and stirred for an additional 2 h at room temperature under an atmosphere of nitrogen. Saturated aqueous NaHCO3 solution was added and the mixture stirred until gas evolution ceased. The mixture was diluted with EtOAc, and the separated aqueous layer was saturated with NaCl and extracted into EtOAc once more. The combined organics were dried over Na2SO4, filtered, and concentrated in vacuo to afford the product.

Workup

  1. stirringstirred for an additional 2 h at room temperature under an atmosphere of nitrogen
  2. stirringthe mixture stirred until gas evolution
  3. extractionextracted into EtOAc once more
  4. dry with materialThe combined organics were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto afford the product

Sources & evidence

ORD record
ord-b4dda52a205342519029fc0bb30dea31
Source dataset
uspto-grants-2008_10
Patent number
US07435735B2

Reaction notes

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