Succinic anhydride → (R/S)-1-(1-adamantyl)methyl-2-(2-carboxyethyl)carbonyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole

HRID 1106933Notes

Reaction equation

HRID 1106933 reaction equation
[C:1]12([CH2:11][CH:12]3[C:17]4[NH:18][C:19]5[C:24]([C:16]=4[CH2:15][CH2:14][NH:13]3)=[CH:23][CH:22]=[CH:21][CH:20]=5)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[C:25]1(=[O:31])[O:30][C:28](=[O:29])[CH2:27][CH2:26]1>O1CCOCC1>[C:1]12([CH2:11][CH:12]3[C:17]4[NH:18][C:19]5[C:24]([C:16]=4[CH2:15][CH2:14][N:13]3[C:25]([CH2:26][CH2:27][C:28]([OH:30])=[O:29])=[O:31])=[CH:23][CH:22]=[CH:21][CH:20]=5)[CH2:10][CH:5]3[CH2:4][CH:3]([CH2:9][CH:7]([CH2:6]3)[CH2:8]1)[CH2:2]2

Participants

4

Reactant 2

HCID 7922Succinic anhydrideHCID 53933490(R/S)-1-(1-adamantyl)methyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole

Product 1

HCID 53950661(R/S)-1-(1-adamantyl)methyl-2-(2-carboxyethyl)carbonyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of (R/S)-1-(1-adamantyl)methyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole (640 mg, 2.0 mmol) and succinic anhydride (250 mg, 2.5 mmol) was stirred in dioxan (5 ml) at room temperature for 17 hours. The white precipiate which had formed was isolated by filtration, washed with dioxan and dried. (640 mg, 76%).

Workup

  1. customThe white precipiate which had formed
  2. customwas isolated by filtration
  3. washwashed with dioxan
  4. customdried

Sources & evidence

ORD record
ord-0532127899f14e8aba970fd530a877ab
Source dataset
uspto-grants-2000_05
Patent number
US06057311

Reaction notes

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