Acetic Acid → tert-Butyl (2-{[(5-cyano-2,3-dihydro-1H-inden-2-yl)methyl]amino}ethyl)carbamate

HRID 1466041Notes

Reaction equation

HRID 1466041 reaction equation
[C:1]([O:5][C:6](=[O:11])[NH:7][CH2:8][CH2:9][NH2:10])([CH3:4])([CH3:3])[CH3:2].[BH3-]C#N.[Na+].CC(O)=O.[CH:20]([CH:22]1[CH2:30][C:29]2[C:24](=[CH:25][CH:26]=[C:27]([C:31]#[N:32])[CH:28]=2)[CH2:23]1)=O.C([O-])([O-])=O.[Na+].[Na+]>CO>[C:31]([C:27]1[CH:28]=[C:29]2[C:24](=[CH:25][CH:26]=1)[CH2:23][CH:22]([CH2:20][NH:10][CH2:9][CH2:8][NH:7][C:6](=[O:11])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3])[CH2:30]2)#[N:32]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 10340Sodium CarbonateHCID 187201N-BOC-ethylenediamineHCID 5003444Sodium cyanoborohydrideHCID 724441512-Formyl-2,3-dihydro-1H-indene-5-carbonitrile

Product 1

HCID 131732678tert-Butyl (2-{[(5-cyano-2,3-dihydro-1H-inden-2-yl)methyl]amino}ethyl)carbamate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of (2-amino-ethyl)-carbamic acid tert-butyl ester (400 mg, 2.5 mmol), NaBH3CN (315 mg, 5.0 mmol) and HOAc (300 mg, 5.0 mmol) in 30 mL MeOH was added 2-formyl-2,3-dihydro-1H-indene-5-carbonitrile (430 mg, 2.5 mmol). The mixture was stirred at RT overnight, and then sat. Na2CO3 (50 mL) was added and stirred for 30 min. The mixture was extracted with EtOAc (3×50 mL) and the combined organic layers were washed with water and brine, dried over anhydrous sodium sulfate and concentrated. The residue was purified by prep-TLC to give the title compound.

Workup

  1. stirringstirred for 30 min
  2. extractionThe mixture was extracted with EtOAc (3×50 mL)
  3. washthe combined organic layers were washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by prep-TLC

Sources & evidence

ORD record
ord-21d92fc47f2f4c81b8cdae6241ab7874
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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