Boc-L-Pro-Ome → (S)-(-)-N-Boc-prolinol

HRID 620151Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 620151
C[O:2][C:3](=O)[C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].[BH4-].[Li+].CO.C(Cl)(Cl)Cl>COCCOC>[C:12]([O:11][C:9]([N:5]1[CH2:6][CH2:7][CH2:8][C@H:4]1[CH2:3][OH:2])=[O:10])([CH3:15])([CH3:13])[CH3:14]

Komponenten

5

Edukt 3

HCID 1277666Boc-L-Pro-OmeHCID 4148881Lithium borohydrideHCID 21584188Chloroform methanol

Produkt 1

HCID 643448(S)-(-)-N-Boc-prolinolAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

This compound was prepared in 92% yield from the ester 4g (9.2 g, 40 mmol) by reduction with lithium borohydride in dry DME following the procedure that has been described earlier1,2. TLC Rf 0.81 (eluent MeOH/CHCl3, 7/93). 1H NMR (CDCl3) δ 1.47 (s, 9H, t-Bu), 1.58-2.18 (m, 4H, CH2CH2CH), 3.15-3.66 (m, 4H, CH2N, CH2OH), 3.73-4.07 (m, 1H, CHN), 4.40-4.80 (br s, 1H, OH).

Quellen und Nachweise

ORD-Eintrag
ord-0cd2346b6f7048a298fb9b154d549979
Quelldatensatz
uspto-grants-1989_04
Patentnummer
US04820712

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