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

HRID 1929078Notes

Reaction equation

HRID 1929078 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>C(OCC)(=O)C.CN(C1C=CN=CC=1)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×

Conditions

Temperature
0 °C

Procedure

4-Benzyloxy-1H-indole-2-carboxylic acid ethyl ester (50 g, 169.3 mmol) is dissolved in 500 ml of ethyl acetate and DMAP (141 mg, 3.4 mmol) is added. Then the mixture is cooled to 0° C. and BOC2O (36.9 g, 169.3 mmol), dissolved in 20 ml of ethyl acetate, is added dropwise. After completion of addition the reaction mixture is allowed to stir over night at room temperature. The mixture is washed with 1M tartaric acid and brine. The organic layers are dried over sodium sulfate and evaporated

Workup

  1. additionis added dropwise
  2. additionAfter completion of addition the reaction mixture
  3. washThe mixture is washed with 1M tartaric acid and brine
  4. dry with materialThe organic layers are dried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-6d148e3be6994a82b3c8d9dff3ce0be0
Source dataset
uspto-grants-2012_05
Patent number
US08183366B2

Reaction notes

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