Diethyl Ether → HCID 13243481, compound

HRID 1762959Notes

Reaction equation

HRID 1762959 reaction equation
C([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[C:12]([C:15](=[O:29])[CH2:16][N:17]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:18]([CH3:21])([CH3:20])[CH3:19])[CH:11]=[CH:10][C:9]=2[O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=O)C.O1CCCC1.C(OCC)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O>[CH2:22]([N:17]([CH2:16][CH:15]([C:12]1[CH:11]=[CH:10][C:9]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[C:8]2[C:13]=1[CH:14]=[C:6]([CH2:4][OH:3])[NH:7]2)[OH:29])[C:18]([CH3:20])([CH3:19])[CH3:21])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8028TetrahydrofuranHCID 13243446HCID 13243446, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 13243481HCID 13243481, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4 g of 7-benzyloxy-4-(N-benzyl-N-tert-butylaminoacetyl)-2-indolecarboxylic acid ethyl ester is combined with 75 ml of absolute tetrahydrofuran and 150 ml of diethyl ether and stirred under ice cooling for 9 hours with 1.2 g of lithium aluminum hydride. Then a small amount of water is added to the reaction mixture, the precipitate is vacuum-filtered, washed with ethyl acetate/diethyl ether, the combined filtrates are concentrated, and the residue is recrystallized from diisopropyl ether, thus obtaining 3.4 g of 2-(N-benzyl-N-tert-butylamino) -1-(7-benzyloxy-2-hydroxymethylindol-4-yl)ethanol, mp 135.5°-136.5° C.

Workup

  1. filtrationthe precipitate is vacuum-filtered
  2. washwashed with ethyl acetate/diethyl ether
  3. concentrationthe combined filtrates are concentrated
  4. customthe residue is recrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-37777c307f864a22b679b56faeeb8027
Source dataset
uspto-grants-1989_05
Patent number
US04835175

Reaction notes

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