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

HRID 1929190Notes

Reaction equation

HRID 1929190 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-1490cd015bf1433ab46d71b5b4ccd11c
Source dataset
uspto-grants-2012_05
Patent number
US08183366B2

Reaction notes

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