Hydrochloric Acid → (R)-3-Ethoxycarbonylamino-pyrrolidine-1-carboxylic acid adamantan-2-ylester

HRID 1948699

Reaktionsgleichung

Reaktionsgleichung von HRID 1948699
Cl.[NH2:2][C@@H:3]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH:11]2[CH:18]3[CH2:19][CH:14]4[CH2:15][CH:16]([CH2:20][CH:12]2[CH2:13]4)[CH2:17]3)=[O:9])[CH2:4]1.CCN(C(C)C)C(C)C.Cl[C:31]([O:33][CH2:34][CH3:35])=[O:32].Cl>C(Cl)Cl>[CH2:34]([O:33][C:31]([NH:2][C@@H:3]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH:11]2[CH:12]3[CH2:13][CH:14]4[CH2:15][CH:16]([CH2:17][CH:18]2[CH2:19]4)[CH2:20]3)=[O:9])[CH2:4]1)=[O:32])[CH3:35]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 10928Ethyl chloroformateHCID 81531DiisopropylethylamineHCID 67155574(R)-2-adamantyl 3-aminopyrrolidine-1-carboxylate HCl salt

Produkt 1

HCID 44473368(R)-3-Ethoxycarbonylamino-pyrrolidine-1-carboxylic acid adamantan-2-ylesterAusbeute 71,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A 1.5 dram vial equipped with a flea stirbar was charged with (R)-2-adamantyl 3-aminopyrrolidine-1-carboxylate HCl salt (30 mg, 0.10 mmol), i-Pr2NEt (72 μL, 0.4 mmol) and CH2Cl2 (1 mL). Ethyl chloroformate (15 mL, 0.123 mmol) was added. The mixture was stirred at rt overnight and applied to a 10-mL Chem-Elut cartridge prewetted with 5% aq HCl (6 mL). The cartridge was eluted with ether (20 mL). The eluate was evaporated to dryness and the residue was purified by prep HPLC to afford (R)-(2-adamantyl) 3-(ethoxycarbonylamino)pyrrolidine-1-carboxylate (24 mg, 71%). LC-MS Method 1 tR=1.88 min, m/z=337; 1H NMR (CDCl3) 1.27 (t, 3H), 1.58 (d, 2H), 1.70-2.00 (13H), 2.19 (m, 1H), 3.13 (1H), 3.26 (dd, 1H), 3.59 (m, 2H), 3.70 (m, 1H), 4.17 (d, 1H), 4.29 (1H), 4.78 (1H), 4.82 (s, 1H)

Aufarbeitung

  1. customA 1.5 dram vial equipped with a flea stirbar
  2. washThe cartridge was eluted with ether (20 mL)
  3. customThe eluate was evaporated to dryness
  4. customthe residue was purified by prep HPLC

Quellen und Nachweise

ORD-Eintrag
ord-468abe4565304ee4bfc61eea254acadd
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399504B2

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