1,2-Dichloroethane → N-t-Butoxycarbonyl-5-[(pyrrolidin-1-yl)carbonyl]isoindoline

HRID 268715Notes

Reaction equation

HRID 268715 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:17]([OH:19])=O)[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)CCl.[CH2:24]([N:26](CC)[CH2:27][CH3:28])[CH3:25].N1CCCC1>C(Cl)Cl.C1C=NC2N(O)N=NC=2C=1>[C:1]([O:5][C:6]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:17]([N:26]3[CH2:27][CH2:28][CH2:25][CH2:24]3)=[O:19])[CH:14]=2)[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 31268PyrrolidineHCID 164501432-(tert-Butoxycarbonyl)-2,3-dihydro-1H-isoindole-5-carboxylic acid

Product 1

HCID 17986289N-t-Butoxycarbonyl-5-[(pyrrolidin-1-yl)carbonyl]isoindoline

Reagents, catalysts & solvents 2

HCID 181649HOAtCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of N-t-butoxycarbonyl-5-carboxyisoindoline (D13) (300 mg), EDC (440 mg), HOAT (10 mg), triethylamine (0.4 ml) and pyrrolidine (0.11 ml) in DCM (10 ml) was stirred overnight and then evaporated. The residue was redissolved in EtOAc (10 ml), washed with saturated NaHCO3 solution (10 ml), water (10 ml), brine (10 ml), dried (MgSO4) and evaporated. The residue was chromatographed on a silica gel flash column [step gradient 70-90% EtOAc in light petroleum 40-60] to give the tiUe compound (D17) (314 mg). MS electrospray (+ion) 317 (MH+). 1H NMR δ (CDCl3): 7.42 (2H, m), 7.27 (1H, m), 4.70 (2H, m), 4.67 (2H, m), 3.65 (2H, m), 3.42 (2H, m), 1.92 (4H, m), 1.52

Workup

  1. customevaporated
  2. dissolutionThe residue was redissolved in EtOAc (10 ml)
  3. washwashed with saturated NaHCO3 solution (10 ml), water (10 ml), brine (10 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residue was chromatographed on a silica gel flash column [step gradient 70-90% EtOAc in light petroleum 40-60]

Sources & evidence

ORD record
ord-eaf4a13f3987408dbfe953577a68dc63
Source dataset
uspto-grants-2008_11
Patent number
US07446103B2

Reaction notes

Loading…