3-(Dimethylamino)-8-ethoxycarbonyl-1,2,3,4-tetrahydrocarbazole → 3-(Dimethylamino)-8-hydroxymethyl-1,2,3,4-tetrahydrocarbazole

HRID 128112Notes

Reaction equation

HRID 128112 reaction equation
[CH3:1][N:2]([CH3:21])[CH:3]1[CH2:15][C:14]2[C:13]3[C:8](=[C:9]([C:16](OCC)=[O:17])[CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[CH2:5][CH2:4]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH3:1][N:2]([CH3:21])[CH:3]1[CH2:15][C:14]2[C:13]3[C:8](=[C:9]([CH2:16][OH:17])[CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 128917873-(Dimethylamino)-8-ethoxycarbonyl-1,2,3,4-tetrahydrocarbazoleHCID 21226445Aluminium lithium hydride

Product 1

HCID 128918683-(Dimethylamino)-8-hydroxymethyl-1,2,3,4-tetrahydrocarbazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following a procedure similar to that described in Example 55 and using 2.4 g. of 3-(dimethylamino)-8-ethoxycarbonyl-1,2,3,4-tetrahydrocarbazole (Example 44), 1,6 g. of lithium aluminum hydride and 150 ml. of dry tetrahydrofuran there was obtained, after successive recrystallizations from isopropyl alcohol and ethyl alcohol, 0.56 g. of 3-(dimethylamino)8-hydroxymethyl-1,2,3,4-tetrahydrocarbazole, m.p. 227°-230° C.

Workup

  1. customafter successive recrystallizations from isopropyl alcohol and ethyl alcohol, 0.56 g

Sources & evidence

ORD record
ord-0ca5219b982e4b47b26d1999badcaf9d
Source dataset
uspto-grants-1981_03
Patent number
US04257952

Reaction notes

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