Sodium Bicarbonate → N-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-5-nitroindan-2-amine

HRID 2088730Notes

Reaction equation

HRID 2088730 reaction equation
C([BH3-])#N.[Na+].S(O)(O)(=O)=O.[N+:10]([C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[CH2:18][CH:17]([NH2:22])[CH2:16]2)([O-:12])=[O:11].[O:23]([CH2:31][CH:32]=O)[Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25].C(=O)(O)[O-].[Na+]>CO>[Si:24]([O:23][CH2:31][CH2:32][NH:22][CH:17]1[CH2:16][C:15]2[C:19](=[CH:20][CH:21]=[C:13]([N+:10]([O-:12])=[O:11])[CH:14]=2)[CH2:18]1)([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25]

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 41877882-((Tert-butyldimethylsilyl)oxy)acetaldehydeHCID 5003444Sodium cyanoborohydrideHCID 160838115-Nitro-2,3-dihydro-1H-inden-2-amine sulfate

Product 1

HCID 58289869N-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-5-nitroindan-2-amineYield 64%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

0.91 g of sodium cyanoborohydride was added to a methanol (100 mL) solution of 2 g of 5-nitroindan-2-amine sulfate and 1.9 g of (tert-butyldimethylsiloxy)acetaldehyde, and stirred at room temperature for 2 days. The reaction liquid was neutralized with aqueous saturated sodium bicarbonate solution, and methanol was evaporated away under reduced pressure. The residue was diluted with water, and extracted three times with chloroform. The organic layer was dried with anhydrous magnesium sulfate, the solvent was evaporated away under reduced pressure, and the crude product was purified through silica gel column chromatography (hexane/ethyl acetate) to obtain 1.56 g of the entitled compound as a yellow oil.

Workup

  1. customThe reaction liquid
  2. customwas evaporated away under reduced pressure
  3. additionThe residue was diluted with water
  4. extractionextracted three times with chloroform
  5. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  6. customthe solvent was evaporated away under reduced pressure
  7. customthe crude product was purified through silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-d56af1afab2046bb97dec5633142f664
Source dataset
uspto-grants-2013_05
Patent number
US08436004B2

Reaction notes

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