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

HRID 1618613ノート

反応式

HRID 1618613 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-0d223cabc6c04c0bb94ccfbbe3167366
出典データセット
uspto-grants-2014_07
特許番号
US08765940B2

反応ノート

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