Red-Al → 4-(3,3,7-Trimethylindolin-6-yl)morpholine

HRID 1618613Notes

Reaction equation

HRID 1618613 reaction equation
[CH3:1][C:2]1([CH3:19])[C:10]2[C:5](=[C:6]([CH3:17])[C:7]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)=[CH:8][CH:9]=2)[NH:4][C:3]1=O.COCCO[AlH2-]OCCOC.[Na+]>C1(C)C=CC=CC=1>[CH3:1][C:2]1([CH3:19])[C:10]2[C:5](=[C:6]([CH3:17])[C:7]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)=[CH:8][CH:9]=2)[NH:4][CH2:3]1

Participants

4

Reactant 2

HCID 16684438Red-AlHCID 672854763,3,7-Trimethyl-6-morpholinoindolin-2-one

Product 1

HCID 672846634-(3,3,7-Trimethylindolin-6-yl)morpholineYield 76.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 3,3,7-trimethyl-6-morpholinoindolin-2-one (45.7 mg, 0.176 mmol) in toluene (10 mL) at 80° C. under N2, Red-Al (0.18 mL, 3M, 0.53 mmol) was added dropwise. The resultant mixture was stirred at 80° C. for 2 h. The mixture was cooled to rt and quenched with NaOH (2 mL, 3N). The mixture was diluted with EtOAc and washed with water and brine, dried and concentrated. Purification of the residue by flash chromatography over silica gel, using 40% EtOAc in hexane, gave 4-(3,3,7-trimethylindolin-6-yl)morpholine (33.1 mg, 76%): 1H-NMR (DMSO-d6) δ 6.74 (1H, d, J=8.0 Hz), 6.29 (1H, d, J=8.0 Hz), 5.11 (1H, s), 3.69 (4H, s), 3.16 (2H, s), 2.72 (4H, s), 1.96 (3H, s), 1.18 (6H, s). Mass Spectrum (ESI) m/e=247.1 (M+1).

Workup

  1. customquenched with NaOH (2 mL, 3N)
  2. additionThe mixture was diluted with EtOAc
  3. washwashed with water and brine
  4. customdried
  5. concentrationconcentrated
  6. customPurification of the residue by flash chromatography over silica gel

Sources & evidence

ORD record
ord-0d223cabc6c04c0bb94ccfbbe3167366
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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