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Acetic Acid → tert-butyl [(1S,2R,3S)-1-benzyl-3-cyclopropyl-2,3-dihydroxypropyl]carbamate

HRID 275628
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 275628
[CH2:1]([C@H:8]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[C@H:9]([C:11]([CH:13]1[CH2:15][CH2:14]1)=[O:12])[OH:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C.[BH4-].[Na+]>C(Cl)Cl>[CH2:1]([C@H:8]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:21])([CH3:20])[CH3:22])[C@@H:9]([OH:10])[C@H:11]([CH:13]1[CH2:15][CH2:14]1)[OH:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 86747482tert-butyl [(1S,2R)-1-benzyl-2-(cyclopropylcarbonyl)-2-hydroxyethyl]carbamate

Produkt 1

HCID 56984559tert-butyl [(1S,2R,3S)-1-benzyl-3-cyclopropyl-2,3-dihydroxypropyl]carbamateAusbeute 74,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

2.83 g (8.77 mmol) tert-butyl [(1S,2R)-1-benzyl-2-(cyclopropylcarbonyl)-2-hydroxyethyl]carbamate were dissolved in 130 ml of methylene chloride, 3 ml of acetic acid were added thereto and the mixture was finally treated portionwise at 0°-10° C. with 0.332 g (8.78 mmol) of sodium borohydride. The reaction solution was stirred at 50 for a further 2 hours and was then partitioned between 2N sodium hydrogen carbonate solution and methylene chloride. The organic phase was separated, washed with water and with saturated sodium chloride solution, dried over magnesium sulphate, filtered and evaporated under reduced pressure. Crystallization of the residue from ether/hexane yielded 2.1 g of tert-butyl [(1S,2R,3S)-1-benzyl-3-cyclopropyl-2,3-dihydroxypropyl]carbamate as colourless needles, m.p. 83-85°.

Aufarbeitung

  1. customwas then partitioned between 2N sodium hydrogen carbonate solution and methylene chloride
  2. customThe organic phase was separated
  3. washwashed with water and with saturated sodium chloride solution
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customCrystallization of the residue from ether/hexane

Quellen und Nachweise

ORD-Eintrag
ord-851141cf5ff749208402cc1612f1fa39
Quelldatensatz
uspto-grants-1995_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05393875

Notizen zur Reaktion

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