D-1,2,3,4-Tetrahydronorharman-3-carboxylic acid → ethyl (3R)-1H,2H,3H,4H,9H-pyrido[3,4-b]indole-3-carboxylate

Reaction equation

[CH2:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH2:4][C@@H:3]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[NH:2]1.C1C2NC3C(=CC=CC=3)C=2C[C@H](C(O)=O)N1>>[CH2:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH2:4][C@H:3]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[NH:2]1

Participants

Reactant 2

HCID 675102D-1,2,3,4-Tetrahydronorharman-3-carboxylic acid

HCID 1079579ethyl (3S)-1H,2H,3H,4H,9H-pyrido[3,4-b]indole-3-carboxylate

Product 1

HCID 7223904ethyl (3R)-1H,2H,3H,4H,9H-pyrido[3,4-b]indole-3-carboxylateYield 54%

Procedure

In the same manner as described above (1) using (3R)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid, there is obtained the title compound (54%) as colorless needles, m.p. 126°-128° C.

Sources & evidence

ORD record: ord-a20e568fc46745fda79e67da936dd249
Source dataset: uspto-grants-1986_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04628057

Reaction notes

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