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

HRID 1106932

Reaction equation

FC(F)(F)C(O)=O.[NH2:8][CH2:9][CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1.[C:20]12([CH2:30][CH:31]=O)[CH2:29][CH:24]3[CH2:25][CH:26]([CH2:28][CH:22]([CH2:23]3)[CH2:21]1)[CH2:27]2>C(Cl)Cl>[C:20]12([CH2:30][CH:31]3[C:12]4[NH:13][C:14]5[C:19]([C:11]=4[CH2:10][CH2:9][NH:8]3)=[CH:18][CH:17]=[CH:16][CH:15]=5)[CH2:21][CH:22]3[CH2:28][CH:26]([CH2:25][CH:24]([CH2:23]3)[CH2:29]1)[CH2:27]2

Participants

Conditions

Temperature: 0 °C

Procedure

Trifluoroacetic acid (443 μl, 5.8 mmol) was added to a solution of tryptamine (5.76 g, 36 mmol) and 1-adamantylacetaldehyde (6.52 g, 36.6 mmol) in dry DCM (450 ml) wth 3A molecular sieves (46.5 g) at 0° C. The reaction mixture was stirred at 0° C. for 2 hours, followed by the addition of trifluoroacetic acid (5.76 ml, 74.8 mmol) then allowed to warm to room temperature and stirring continued for a further 16 hours. The resultant suspension was concentrated in vacuo, taken up in ethyl acetate (200 ml), filtered, washed successively with saturated NaHCO3 solution (200 ml), brine (2×200 ml) and dried (MgSO4). Filtration and evaporation of the solvent gave the crude product as an orange foam which was used without further purification. (10.95 g, 95%).

Workup

temperatureto warm to room temperature
stirringstirring
waitcontinued for a further 16 hours
concentrationThe resultant suspension was concentrated in vacuo
filtrationfiltered
washwashed successively with saturated NaHCO3 solution (200 ml), brine (2×200 ml)
dry with materialdried (MgSO4)
filtrationFiltration and evaporation of the solvent

Sources & evidence

ORD record: ord-52e02d18810840879caff7db30fc6329
Source dataset: uspto-grants-2000_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06057311

Linked notes

Loading…