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

HRID 1618613노트

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HRID 1618613 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-0d223cabc6c04c0bb94ccfbbe3167366
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08765940B2

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