Trifluoroacetic acid → (1R,3S)-benzyl 1-(1-adamantyl)methyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]-indole-3-carboxylate

HRID 1106929Notes

Reaction equation

HRID 1106929 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([O:15][C:16](=[O:29])[C@H:17]([CH2:19][C:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[NH:22][CH:21]=1)[NH2:18])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[C:30]12([CH2:40][CH:41]=O)[CH2:39][CH:34]3[CH2:35][CH:36]([CH2:38][CH:32]([CH2:33]3)[CH2:31]1)[CH2:37]2.C(OCC)(=O)C.C(Cl)Cl>C(Cl)Cl>[C:30]12([CH2:40][C@@H:41]3[C:21]4[NH:22][C:23]5[C:28]([C:20]=4[CH2:19][C@@H:17]([C:16]([O:15][CH2:8][C:9]4[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=4)=[O:29])[NH:18]3)=[CH:27][CH:26]=[CH:25][CH:24]=5)[CH2:31][CH:32]3[CH2:38][CH:36]([CH2:35][CH:34]([CH2:33]3)[CH2:39]1)[CH2:37]2

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acid2×HCID 50860842-(Adamantan-1-yl)acetaldehydeHCID 7016092L-Tryptophan benzyl esterHCID 21226138Dichloromethane ethylacetate

Product 1

HCID 10551689(1R,3S)-benzyl 1-(1-adamantyl)methyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]-indole-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (270 μl, 3.5 mmol) was added to a solution of L-tryptophan benzyl ester (10.23 g, 34.8 mmol) and 1-adamantylacetaldehyde (6.2 g, 34.8 mmol) in dry DCM (300 ml) wth 3A molecular sieves (46.5 g) at -10° C. The reaction mixture was allowed to warm to room temperature and stirred for 7 hours. The mixture was cooled to 0° C. trifluoroacetic acid (5.6 ml, 72.7 mmol) added, and stirring continued at room temperature for 16 hours. The reaction mixture was 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. The compound was obtained by isolation of the more polar component by flash chromatography on silica gel with ethyl acetate-DCM (1:40) as eluant. (6.2 g, 39%)

Workup

  1. additionadded
  2. stirringstirring
  3. waitcontinued at room temperature for 16 hours
  4. filtrationThe reaction mixture was filtered
  5. washwashed successively with saturated NaHCO3 solution (200 ml), brine (2×200 ml)
  6. dry with materialdried (MgSO4)
  7. filtrationFiltration and evaporation of the solvent
  8. customgave the crude product

Sources & evidence

ORD record
ord-d3600634d0a145f38dd566702bcc0cb8
Source dataset
uspto-grants-2000_05
Patent number
US06057311

Reaction notes

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