Dimethylamine → HCID 86692849, compound

HRID 2271536Notes

Reaction equation

HRID 2271536 reaction equation
O=[C:2]1[C:10]2[C:5](=[CH:6][C:7]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:8][CH:9]=2)[CH2:4][CH2:3]1.[CH3:19][NH:20][CH3:21].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C([O-])(O)=O.[Na+]>[CH3:19][N:20]([CH3:21])[CH:2]1[C:10]2[C:5](=[CH:6][C:7]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:8][CH:9]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 251989431116358-96-3

Product 1

HCID 86692849HCID 86692849, compoundYield 54.3%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of tert-butyl (1-oxo-2,3-dihydro-1H-inden-5-yl)carbamate (371 mg, 1.5 mmol) in dimethylamine (2.0 M solution in THF, 5 mL, 10 mmol) was added sodium triacetoxyborohydride (636 mg, 3.0 mmol). The resultant suspension was stirred at room temperature for 16 h, diluted with a saturated NaHCO3 solution and extracted with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated. Purification by column chromatography (silica, 0-20% methanol/dichloromethane) afforded the desired product (225 mg, 54%) as an off-white solid. ESI MS m/z 277 [C16H24N2O2+H]+

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customPurification by column chromatography (silica, 0-20% methanol/dichloromethane)

Sources & evidence

ORD record
ord-d306147bd92f4450a9a779bb2a5096d8
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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