1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → rac-(2-{[2-((1R*,2R*,4R*)-2-hydroxy-5-phenyl-bicyclo[2.2.2]oct-5-en-2-yl)-ethyl]-methyl-carbamoyl}-ethyl)-carbamic acid tert.-butyl ester

HRID 220316

Reaktionsgleichung

Reaktionsgleichung von HRID 220316
[C:1]([NH:8][CH2:9][CH2:10][C:11]([OH:13])=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.[CH3:33][NH:34][CH2:35][CH2:36][C:37]1([OH:51])[CH2:42][CH:41]2[CH2:43][CH2:44][CH:38]1[CH:39]=[C:40]2[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1.CCN=C=NCCCN(C)C>C(Cl)Cl>[C:4]([O:3][C:1](=[O:2])[NH:8][CH2:9][CH2:10][C:11](=[O:13])[N:34]([CH2:35][CH2:36][C@:37]1([OH:51])[CH2:42][C@H:41]2[CH2:43][CH2:44][C@@H:38]1[CH:39]=[C:40]2[C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1)[CH3:33])([CH3:5])([CH3:6])[CH3:7]

Komponenten

7

Edukt 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 76809N-((1,1-dimethylethoxy)carbonyl)-beta-alanineHCID 81531DiisopropylethylamineHCID 68415512rac-(1R*,2R*,4R*)-2-(2-methylamino-ethyl)-5-phenyl-bicyclo[2.2.2]oct-5-en-2-ol

Produkt 1

HCID 68414834rac-(2-{[2-((1R*,2R*,4R*)-2-hydroxy-5-phenyl-bicyclo[2.2.2]oct-5-en-2-yl)-ethyl]-methyl-carbamoyl}-ethyl)-carbamic acid tert.-butyl esterAusbeute 46,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 159 mg of BOC-beta-alanine in 4 mL DCM were added 0.36 mL DIPEA and 113 mg of HOBt. After stirring for 15 min, 300 mg of rac-(1R*,2R*,4R*)-2-(2-methylamino-ethyl)-5-phenyl-bicyclo[2.2.2]oct-5-en-2-ol in 4 mL DCM were added followed by 161 mg of EDCI. The resulting suspension was stirred for 2 h at rt, then quenched with water. The water phase was reextracted with DCM, the combined organic phases were washed with sat. aq. NaHCO3, dried and concentrated in vacuo. The residue was purified by preparative TLC with EtOAc to give 168 mg of rac-(2-{[2-((1R*,2R*,4R*)-2-hydroxy-5-phenyl-bicyclo[2.2.2]oct-5-en-2-yl)-ethyl]-methyl-carbamoyl}-ethyl)-carbamic acid tert.-butyl ester as white foam.

Aufarbeitung

  1. stirringThe resulting suspension was stirred for 2 h at rt
  2. customquenched with water
  3. washthe combined organic phases were washed with sat. aq. NaHCO3
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by preparative TLC with EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-11d79fce57204723a71b89969c0f1227
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202885B2

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