1,2-Dichloroethane → N-t-Butoxycarbonyl-5-[(morpholin-4-yl)carbonyl]isoindoline

HRID 268716Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 268716
[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.C(N(CC)CC)C.[NH:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1>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:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)=[O:19])[CH:14]=2)[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Komponenten

7

Edukt 4

HCID 111,2-DichloroethaneHCID 8083MorpholineHCID 8471TriethylamineHCID 164501432-(tert-Butoxycarbonyl)-2,3-dihydro-1H-isoindole-5-carboxylic acid

Produkt 1

HCID 17986287N-t-Butoxycarbonyl-5-[(morpholin-4-yl)carbonyl]isoindoline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 181649HOAtKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of N-t-butoxycarbonyl-5-carboxyisoindoline (D13) (300 mg), EDC (440 mg), HOAT (10 mg), triethylamine (0.4 ml) and morpholine (0.12 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 title compound (D19) (314 mg). MS electrospray (+ion) 333 (MH+). 1H NMR δ (CDCl3): 7.30 (3H, m), 4.70 (2H, m), 4.67 (2H, m), 3.70 (8H, m), 1.52 (9H, s).

Aufarbeitung

  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]

Quellen und Nachweise

ORD-Eintrag
ord-117746c291fb4161a0b17860b2855f4e
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07446103B2

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