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

HRID 966544Notes

Reaction equation

HRID 966544 reaction equation
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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-89d84ae3084f40a0b858cefdeb38e377
Source dataset
uspto-grants-2005_10
Patent number
US06951848B2

Reaction notes

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