Triethylamine → HCID 58593196, compound

HRID 1271717Notes

Reaction equation

HRID 1271717 reaction equation
[NH:1]1[CH2:5][CH:4]=[CH:3][CH2:2]1.CCN(CC)CC.[C:13](Cl)([O:15][CH2:16][CH:17]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]2[C:18]1=[CH:19][CH:20]=[CH:21][CH:22]=2)=[O:14]>C(Cl)Cl>[CH:28]1[C:29]2[CH:17]([CH2:16][O:15][C:13]([N:1]3[CH2:5][CH:4]=[CH:3][CH2:2]3)=[O:14])[C:18]3[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:24]=2[CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 343679-Fluorenylmethyl chloroformateHCID 660593-Pyrroline

Product 1

HCID 58593196HCID 58593196, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-pyrroline (25.0 g, 0.36 mol) in CH2Cl2 (500 mL) at 0° C. was added Et3N (60 mL, 0.42 mol), followed by Fmoc-Cl (103 g, 0.39 mole) at 0° C. The reaction mixture was stirred at 0° C. for 1 h, then 30 minutes at it. The reaction mixture was partitioned between H2O (250 mL) and CH2Cl2 (150 mL×3). The organic phase was washed with brine and dried over Na2SO4. The solvent was evaporated, and the residue was purified on silica gel using 5 to 70% EtOAc in hexanes as eluting solvents to afford 2,5-dihydro-pyrrole-1-carboxylic acid 9H-fluoren-9-ylmethyl ester (99 g, 95%) as a white solid. MS m/z 314.0 ([M+Na]+).

Workup

  1. custom30 minutes
  2. customThe reaction mixture was partitioned between H2O (250 mL) and CH2Cl2 (150 mL×3)
  3. washThe organic phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. customThe solvent was evaporated
  6. customthe residue was purified on silica gel using 5 to 70% EtOAc in hexanes
  7. washas eluting solvents

Sources & evidence

ORD record
ord-2b6d5404d91044868795a9a95382355d
Source dataset
uspto-grants-2007_04
Patent number
US07205318B2

Reaction notes

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