Lithium Chloride → tert-butyl N-[(2S)-1-hydroxy-3-phenylpropan-2-yl]carbamate

HRID 345010Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 345010
[CH3:1][C:2]([CH3:20])([O:4][C:5]([NH:7][C@H:8]([C:16](OC)=[O:17])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:6])[CH3:3].[Cl-].[Li+].[BH4-].[Na+]>O1CCCC1.C(O)C>[CH3:3][C:2]([CH3:20])([O:4][C:5]([NH:7][C@@H:8]([CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[CH2:16][OH:17])=[O:6])[CH3:1]

Komponenten

6

Edukt 3

HCID 433294Lithium ChlorideHCID 4311764Sodium borohydrideHCID 9882138Boc-L-phenylalanine methyl ester

Produkt 1

HCID 2733675tert-butyl N-[(2S)-1-hydroxy-3-phenylpropan-2-yl]carbamateAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution containing N-[(1,1-dimethylethoxy)carbonyl]-L-phenylalanine, methyl ester (10 g, 35.8 mmole) dissolved in a mixture of tetrahydrofuran (190 ml) and absolute ethanol (190 ml) is added lithium chloride (6.09 g, 143.2 mmole). The resulting homogeneous solution is treated with sodium borohydride (5.42 g, 143.2 mmole) and the reaction is stirred at room temperature under argon for 24 hours. The reaction mixture is next filtered using ether (~700 ml) to rinse the filter cake. The resulting filtrate is rinsed with water (3×200 ml) and brine (200 ml), dried over magnesium sulfate, and concentrated in vacuo to give 9 g of crude product. Recrystallization from ether/hexane gives 7.59 g of the title D compound,; m.p. 94°-96°.

Aufarbeitung

  1. filtrationThe reaction mixture is next filtered
  2. washto rinse the filter cake
  3. washThe resulting filtrate is rinsed with water (3×200 ml) and brine (200 ml)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-089d1eaba0344d5fb0e917683340662d
Quelldatensatz
uspto-grants-1991_10
Patentnummer
US05055466

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