Methanol → (2s,4r)-4-(n-Tert-butoxycarbonylglycylamino)-2-hydroxymethyl-n-tert-butoxycarbonylpyrrolidine

HRID 2185488Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2185488
CO.[C:3]([O:7][C:8]([NH:10][CH2:11][C:12]([NH:14][C@H:15]1[CH2:19][N:18]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C@H:17]([C:27](O)=[O:28])[CH2:16]1)=[O:13])=[O:9])([CH3:6])([CH3:5])[CH3:4].[BH4-].[Li+].O>O1CCCC1>[C:3]([O:7][C:8]([NH:10][CH2:11][C:12]([NH:14][C@H:15]1[CH2:19][N:18]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C@H:17]([CH2:27][OH:28])[CH2:16]1)=[O:13])=[O:9])([CH3:4])([CH3:6])[CH3:5]

Komponenten

6

Edukt 4

HCID 887MethanolHCID 962WaterHCID 4148881Lithium borohydrideHCID 21341559trans-4-(N-tert-butoxycarbonylglycyl)amino-N-tert-butoxycarbonyl-L-proline

Produkt 1

HCID 70172939(2s,4r)-4-(n-Tert-butoxycarbonylglycylamino)-2-hydroxymethyl-n-tert-butoxycarbonylpyrrolidineAusbeute 97,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Methanol (8 mL) was added over a period of 1 hr to a refluxed mixture of trans-4-N-tert-butoxycarbonylglycylamino)-N-tert-butoxycarbonyl-L-proline methyl ester (Compound D103 (B), 1.39 g) and lithium borohydride (328 mg) in tetrahydrofuran (30 mL). After being cooled, water was added to the mixture and the product was extracted twice with chloroform. The combined organic layers were dried over anhydrous sodium sulfate, then evaporated in vacuo and the residue was purified by silica gel column chromatography (chloroform:methanol=95:5, v/v) to give title compound (1.31 g): 1H NMR (400 MHz, CDCl3) δ 1.46 (s, 9H), 1.47 (s, 9H), 1.89 (m, 1H), 1.98 (m, 1H), 3.34 (dd, J=11.7, 3.9 Hz, 1H), 3.60 (d, J=5.9 Hz, 1H), 3.64 (d, J=5.9 Hz, 1H), 3.69 (m, 1H), 3.75 (d, J=5.9 Hz, 1H), 4.04 (m, 1H), 4.42 (m, 1H), 4.55 (m, 1H), 5.15 (m, 1H), and 6.44 (m, 1H).

Aufarbeitung

  1. temperatureAfter being cooled
  2. extractionthe product was extracted twice with chloroform
  3. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  4. customevaporated in vacuo
  5. customthe residue was purified by silica gel column chromatography (chloroform

Quellen und Nachweise

ORD-Eintrag
ord-8081b9b314fd4fe58dfad07b0b181a98
Quelldatensatz
uspto-grants-2002_06
Patentnummer
US06399629B1

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