Sodium borohydride → N-(4-hydroxy-1-adamantyl)acetamide

HRID 72114

Reaktionsgleichung

Reaktionsgleichung von HRID 72114
[C:1]([NH:4][C:5]12[CH2:14][CH:9]3[CH2:10][CH:11]([CH2:13][CH:7]([C:8]3=[O:15])[CH2:6]1)[CH2:12]2)(=[O:3])[CH3:2].[BH4-].[Na+]>CO>[C:1]([NH:4][C:5]12[CH2:14][CH:9]3[CH2:10][CH:11]([CH2:13][CH:7]([CH:8]3[OH:15])[CH2:6]1)[CH2:12]2)(=[O:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 5338964N-(4-oxo-1-adamantyl)acetamide

Produkt 1

HCID 14948121N-(4-hydroxy-1-adamantyl)acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A stirred solution of 1-acetamido-4-oxoadamantane (420 mg, 2.0 mmol) in MeOH (20 mL) was cooled in an ice bath and an NaBH4 caplet (1.0 g, 26 mmol) was added. The mixture was stirred over the weekend at rt and evaporated to dryness. The residue was taken up in EtOAc (90 mL), washed with 5% aq HCl (20 mL) and satd aq NaHCO3 (20 mL), and dried over MgSO4. Removal of the solvent left 1-acetamido-4-hydroxyadamantane (170 mg, 40%).

Aufarbeitung

  1. customevaporated to dryness
  2. washwashed with 5% aq HCl (20 mL)
  3. dry with materialdried over MgSO4
  4. customRemoval of the solvent
  5. waitleft 1-acetamido-4-hydroxyadamantane (170 mg, 40%)

Quellen und Nachweise

ORD-Eintrag
ord-b18a689529254733af5ff770d15b2ced
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08828985B2

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