4-Methylmorpholine → ethyl (1R,2S)-2-[(1H-indol-2-ylcarbonyl)amino]cyclohexane-carboxylate

HRID 1883109Notes

Reaction equation

HRID 1883109 reaction equation
Br.[NH2:2][C@H:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C@H:4]1[C:9]([O:11][CH2:12][CH3:13])=[O:10].[NH:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[C:15]1[C:23](O)=[O:24].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>CN(C=O)C>[NH:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[C:15]1[C:23]([NH:2][C@H:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C@H:4]1[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:24]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 72899Indole-2-carboxylic acidHCID 757711-HydroxybenzotriazoleHCID 122236269Ethyl (1R,2S)-2-aminocyclohexane-1-carboxylate hydrobromide

Product 1

HCID 71206173ethyl (1R,2S)-2-[(1H-indol-2-ylcarbonyl)amino]cyclohexane-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 300 mg (1.19 mmol) of ethyl (1R,2S)-2-aminocyclohexanecarboxylate HBr 10 salt (Xu, Daquiang et al., Tetrahedron: Asymmetry (1988), 9(10) 1635) dissolved in 8 mL DMF was added 192 mg (1.19 mmol) of indole-2-carboxylic acid, 228 mg (1.19 mmol) of EDCI, 161 mg (1.19 mmol) of HOBT and 0.458 mL (4.16 mmol) of N-methylmorpholine. The reaction mixture was stirred at room temperature overnight, partitioned between ethyl acetate and water, dried over magnesium sulfate and concentrated to provide ethyl (1R,2S)-2-[(1H-indol-2-ylcarbonyl)amino]cyclohexane-carboxylate.

Workup

  1. custompartitioned between ethyl acetate and water
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-26232273f42e46e78caefac181c7f7ae
Source dataset
uspto-grants-2004_07
Patent number
US06759428B2

Reaction notes

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