Cyclopentanone → 5-(2-Cyclohexylamino-ethyl)-2-methyl-1H-indole-3-carboxylic Acid Benzyl Ester

HRID 966544노트

반응식

HRID 966544 반응식
Cl.[CH2:2]([O:9][C:10]([C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([CH2:21][CH2:22][NH2:23])[CH:19]=2)[NH:14][C:13]=1[CH3:24])=[O:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:25]1(=O)[CH2:29][CH2:28][CH2:27][CH2:26]1.[C:31](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>ClC(Cl)C>[CH2:2]([O:9][C:10]([C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([CH2:21][CH2:22][NH:23][CH:26]3[CH2:27][CH2:28][CH2:29][CH2:25][CH2:31]3)[CH:19]=2)[NH:14][C:13]=1[CH3:24])=[O:11])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

참가 물질

6

반응물 4

HCID 8452CyclopentanoneHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 697397605-(2-Amino-ethyl)-2-methyl-1H-indole-3-carboxylic Acid Benzyl Ester Hydrochloride

생성물 1

HCID 101109815-(2-Cyclohexylamino-ethyl)-2-methyl-1H-indole-3-carboxylic Acid Benzyl Ester

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매

실험 절차

5-(2-Amino-ethyl)-2-methyl-1H-indole-3-carboxylic acid benzyl ester hydrochloride (0.331 g, 0.961 mmol) and cyclopentanone (99.6 μL, 0.961 mmol) were mixed together in dichloroethane and stirred at room temperature under N2 for 30 minutes. The mixture was then cooled to 0° C., whereupon sodium triacetoxyborohydride (0.209 g, 0.988 mmol) was added and stirred without warming for a further 30 minutes). The reaction was then permitted to warm to rt and stirred for 20 hours. 1N NaOH (10 ML) was then added and extracted with EtOAc. The combined organic layers was washed with brine, dried on Na2SO4 and chromatographed (10% MeOH/CH2Cl2) to give 0.200 g, (53%), of the desired product, mp 97-100° C. pure product. 1HNMR (400 MHz, DMSO): δ 0.86-1.73 (m, 10H), 2.31 (m, 1H), 2.59 (s, 3H, ArCH3), 2.69 (m, 4H), 5.29 (s, 2H), 6.93 (d, J=8.06 Hz, J=1.64 Hz, ArH), 7.21 (d, J=8.06 Hz, 1H), 7.28-7.45 (m, 5H, ArH), 7.70 (s, 1H, ArH), 11.74 (s, ArNH). MS (APCI+) m/z 391.2(MH+). Anal. Calcd for C25H30N2O2.0.20H2O: C, 76.19; H, 7.77; N, 7.11. Found: C, 75.84: H, 8.09: N, 6.73. IR (KBr): 3309, 2927, 2854,1662, 1450, 1076 cm−1.

후처리

  1. additionwas added
  2. stirringstirred
  3. temperaturewithout warming for a further 30 minutes)
  4. temperatureto warm to rt
  5. stirringstirred for 20 hours
  6. extractionextracted with EtOAc
  7. washThe combined organic layers was washed with brine
  8. customdried on Na2SO4
  9. customchromatographed (10% MeOH/CH2Cl2)

출처 및 근거

ORD 기록
ord-89d84ae3084f40a0b858cefdeb38e377
출처 데이터셋
uspto-grants-2005_10
특허 번호
US06951848B2

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