Lithium Hydroxide → (2S,3R)-1-[(tert-Butoxy)carbonyl]-3-methoxypyrrolidine-2-carboxylic acid

HRID 1527322Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1527322
C[O:2][C:3]([C@@H:5]1[C@H:9]([O:10][CH3:11])[CH2:8][CH2:7][N:6]1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[O:4].[Li+].[OH-]>C1COCC1.O>[C:15]([O:14][C:12]([N:6]1[CH2:7][CH2:8][C@@H:9]([O:10][CH3:11])[C@H:5]1[C:3]([OH:4])=[O:2])=[O:13])([CH3:18])([CH3:16])[CH3:17]

Komponenten

5

Edukt 2

HCID 3939Lithium Hydroxide2×HCID 66619640N-BOC-3(R)-methoxy-(L)-proline, methyl ester

Produkt 1

HCID 69351760(2S,3R)-1-[(tert-Butoxy)carbonyl]-3-methoxypyrrolidine-2-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of (2S,3R)-3-methoxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (150 mg, 0.578 mmol) in THF (4 mL) and water (2.0 mL) was added LiOH (69.3 mg, 2.89 mmol) and the reaction mixture was stirred at RT for 40 h. Another aliquot of LiOH was added (69.3 mg, 2.89 mmol). Stirring was continued at RT for 60 h and subsequently at 50° C. for 16 h to complete the reaction. Water was added and volatiles were removed under reduced pressure. The aqueous phase was adjusted to pH 2 to 3 by addition of 1N aqueous HCl, followed by extraction with EtOAC (3×). The combined organics were dried (Phase separator) and concentrated in vacuo to give the title compound as a white solid. MS (LC/MS): 262 [M+Na]+, 190 [MH−tBu]+, 146 [MH−Boc]+, tR (HPLC conditions b): 3.51 min.

Aufarbeitung

  1. stirringStirring
  2. waitwas continued at RT for 60 h and subsequently at 50° C. for 16 h
  3. customthe reaction
  4. customvolatiles were removed under reduced pressure
  5. additionThe aqueous phase was adjusted to pH 2 to 3 by addition of 1N aqueous HCl
  6. extractionfollowed by extraction with EtOAC (3×)
  7. customThe combined organics were dried (Phase separator)
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-84255e7b4aa44ffaa136cd4b2c2e9db0
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09085555B2

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