Triethylamine → HCID 86610077, compound

HRID 1991277Notes

Reaction equation

HRID 1991277 reaction equation
CC1[N:3]([C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[N:13]([C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[C@H:12]([CH3:27])[CH2:11]3)C(C)=CC=1.C(N(CC)CC)C.Cl.NO>O.C(O)C>[NH2:3][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[N:13]([C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])[C@H:12]([CH3:27])[CH2:11]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 86610076HCID 86610076, compound

Product 1

HCID 86610077HCID 86610077, compound

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred solution of phenylmethyl (2R)-5-(2,5-dimethyl-1H-pyrrol-1-yl) -2,3-dihydro-2-methyl-1H-indole-1-carboxylate (Step 3, 2.11 g, 5.84 mmol) in water/ethanol (1:9, 60 mL) is added triethylamine (6.5 mL, 46.7 mmol) and hydroxylamine hydrochloride (6.49 g, 93.4 mmol). The reaction mixture is stirred at 90° C. for 20 h and is then concentrated under reduced pressure. The residue is taken up in CH2Cl2 (60 mL) and washed with H2O (2×20 mL) and saline (2×20 mL), and the combined aqueous layer is extracted with CH2Cl2 (2×20 mL). The combined organic layer is dried over anhydrous sodium sulfate and concentrated under reduced pressure, and the residue is purified by chromatography on a Biotage Flash 40M 90 g silica gel cartridge (30-50% EtOAc/Hexanes eluent) to give the title compound, MS (ESI+) for C17H18N2O2 m/z 283 (M+H)+.

Workup

  1. concentrationis then concentrated under reduced pressure
  2. washwashed with H2O (2×20 mL) and saline (2×20 mL)
  3. extractionthe combined aqueous layer is extracted with CH2Cl2 (2×20 mL)
  4. dry with materialThe combined organic layer is dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customthe residue is purified by chromatography on a Biotage Flash 40M 90 g silica gel cartridge (30-50% EtOAc/Hexanes eluent)

Sources & evidence

ORD record
ord-a1849f3c59344b03bca26db23fee975b
Source dataset
uspto-grants-2010_01
Patent number
US07645781B2

Reaction notes

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