Triethylamine → HCID 70455602, compound

HRID 1732138Notes

Reaction equation

HRID 1732138 reaction equation
[OH:1][CH2:2][C@@H:3]1[CH2:15][C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[CH2:5][NH:4]1.C(N(CC)CC)C.[CH2:23]([O:30][C:31](Cl)=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CO>[CH2:23]([O:30][C:31]([N:4]1[C@H:3]([CH2:2][OH:1])[CH2:15][C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[CH2:5]1)=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 13375506(3S)-3-hydroxymethyl-1,2,3,4-tetrahydro-beta-carboline

Product 1

HCID 70455602HCID 70455602, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.02 g of (3S)-3-hydroxymethyl-1,2,3,4-tetrahydro-β-carboline are dissolved in 24 ml of methanol, and 1.5 ml of triethylamine and 1.8 ml of benzyloxycarbonyl chloride are added dropwise to the mixture. The mixture is stirred at 5°-10° C. for 3 hours, and the mixture is evaporated to remove the solvent. The residue is dissolved in ethyl acetate. The solution is washed with water, a 0.5M citric acid solution and water, dried and then evaporated to remove the solvent. 2.90 g of (3S)-2-benzyloxycarbonyl-3-hydroxymethyl-1,2,3,4-tetrahydro-β-carboline are obtained as colorless oil. Yield: 86%

Workup

  1. customthe mixture is evaporated
  2. customto remove the solvent
  3. dissolutionThe residue is dissolved in ethyl acetate
  4. washThe solution is washed with water
  5. dry with materiala 0.5M citric acid solution and water, dried
  6. customevaporated
  7. customto remove the solvent

Sources & evidence

ORD record
ord-d2a7c147ea2e4389b3a1ed482a62513a
Source dataset
uspto-grants-1986_11
Patent number
US04625032

Reaction notes

Loading…