Sodium cyanoborohydride → (R)-3-(1H-Indol-3-ylmethyl)-1-(2-phenyl-ethyl)-2-oxo-piperazine

HRID 356852Notes

Reaction equation

HRID 356852 reaction equation
C(O[C:6]([N:8]([CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:9][CH:10]=O)=[O:7])(C)(C)C.Cl.[NH:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]([CH2:30][C@@H:31]([NH2:36])CC(O)=O)=[CH:22]1.C([BH3-])#N.[Na+]>CO.C1COCC1.C(OCC)(=O)C>[NH:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]([CH2:30][C@H:31]2[NH:36][CH2:10][CH2:9][N:8]([CH2:12][CH2:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:6]2=[O:7])=[CH:22]1

Participants

7

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 23225807N-t-butoxycarbonyl-N-(2-oxo-ethyl)-2-phenyl-ethylamineHCID 51064127(R)-3-Amino-4-(1H-indol-3-yl)butanoic acid hydrochloride

Product 1

HCID 15391969(R)-3-(1H-Indol-3-ylmethyl)-1-(2-phenyl-ethyl)-2-oxo-piperazine

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Combine N-t-butoxycarbonyl-N-(2-oxo-ethyl)-2-phenyl-ethylamine (5.03 g, 19.0 mmol) and (R)-2-(1H-indol-3-yl)-1-carboxymethyl-ethylamine hydrochloride salt ((R)-tryptophan methyl ester hydrochloride salt) (4.9 g, 19.42 mmol) in methanol (50 mL) and stir for 30 minutes. Add sodium cyanoborohydride in solution (15.0 mL, 1M in THF, 15.0 mmol) and stir under an inert atmosphere for 16.5 hours. Concentrate in vacuo to obtain a residue. Dilute the residue with ethyl acetate and extract with water. Separate the layers, dry the organic layer over MgSO4, filter, and evaporate in vacuo. Chromatograph on silica gel eluting with 50% ethyl acetate/hexane to give the title compound.

Workup

  1. concentrationConcentrate in vacuo
  2. customto obtain a residue
  3. extractionextract with water
  4. customSeparate the layers
  5. dry with materialdry the organic layer over MgSO4
  6. filtrationfilter
  7. customevaporate in vacuo

Sources & evidence

ORD record
ord-a80987f40a714dab88f60e6e8ed1c04e
Source dataset
uspto-grants-1998_11
Patent number
US05840726

Reaction notes

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