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Water → tert-Butyl 2-(hydroxymethyl)morpholine-4-carboxylate

HRID 456392
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 456392
[N:1]1([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:6][CH2:5][O:4][CH:3]([C:7](OC)=[O:8])[CH2:2]1.[BH4-].[Li+].O>O1CCCC1>[OH:8][CH2:7][CH:3]1[O:4][CH2:5][CH2:6][N:1]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:2]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 962WaterHCID 4148881Lithium borohydrideHCID 588174744-tert-Butyl 2-methyl morpholine-2,4-dicarboxylate

Produkt 1

HCID 5201202tert-Butyl 2-(hydroxymethyl)morpholine-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

The crude product from step (i) (62.6 mmol) was dissolved in dry tetrahydrofuran (THF) (100 ml) and added dropwise at 0° C. to a suspension of lithium borohydride (2.50 g, 115 mmol) in dry THF (100 ml). The mixture was allowed to attain room temperature over night. Water (10 ml) was added and after stirring for 1 h the mixture was concentrated. The residue was partitioned between ethyl acetate and water. The organic phase was washed with 0.5 M hydrochloric acid, saturated sodium hydrogen carbonate and water. Drying over magnesium sulfate and concentration gave the title compound as a crude product (13.3 g).

Aufarbeitung

  1. waitto attain room temperature over night
  2. concentrationwas concentrated
  3. customThe residue was partitioned between ethyl acetate and water
  4. washThe organic phase was washed with 0.5 M hydrochloric acid, saturated sodium hydrogen carbonate and water
  5. dry with materialDrying over magnesium sulfate and concentration

Quellen und Nachweise

ORD-Eintrag
ord-868578121e3c4fc391be969e260f58bb
Quelldatensatz
uspto-grants-2007_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07186718B2

Notizen zur Reaktion

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