Di-tert-butyl dicarbonate → 1-tert-butyl 2-ethyl 4-(benzyloxy)-1H-indole-1,2-dicarboxylate

HRID 2267897Notes

Reaction equation

HRID 2267897 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[C:12]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH:11]=[CH:10][CH:9]=2)=[O:5])[CH3:2].[O:23](C(OC(C)(C)C)=O)[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=O>CN(C1C=CN=CC=1)C.C(OCC)(=O)C>[CH3:2][CH2:1][O:3][C:4]([C:6]1[N:7]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:23])[C:8]2[C:13]([CH:14]=1)=[C:12]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH:11]=[CH:10][CH:9]=2)=[O:5]

Participants

5

Reactant 2

HCID 90495Di-tert-butyl dicarbonateHCID 119707Ethyl 4-(phenylmethoxy)-1H-indole-2-carboxylate

Product 1

HCID 591526751-tert-butyl 2-ethyl 4-(benzyloxy)-1H-indole-1,2-dicarboxylate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

4-Benzyloxy-1H-indole-2-carboxylic acid ethyl ester (10 g, 34 mmol) and DMAP (80 mg) are dissolved in 80 ml of ethyl acetate. BOC2O (8.9 g, 41 mmol) dissolved in a small amount of ethyl acetate is added at room temperature. The mixture is stirred over night at room temperature. Then the reaction mixture is washed with 1 m aqueous tartaric acid, water and brine. The organic layers are dried over sodium sulfate and evaporated. The crude product is used in the next step without further purification.

Workup

  1. additionis added at room temperature
  2. washThen the reaction mixture is washed with 1 m aqueous tartaric acid, water and brine
  3. dry with materialThe organic layers are dried over sodium sulfate
  4. customevaporated
  5. customThe crude product is used in the next step without further purification

Sources & evidence

ORD record
ord-a205b446310548dbb064922d912f8993
Source dataset
uspto-grants-2010_12
Patent number
US07858781B2

Reaction notes

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