Sodium Hydroxide → tert-butyl N-(2-methyl-1-oxopropan-2-yl)carbamate

HRID 6437

Reaktionsgleichung

Reaktionsgleichung von HRID 6437
[C:1]([NH:8][C:9]([CH3:13])([CH3:12])[CH2:10][OH:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH-].[Na+]>C(Cl)Cl.C(OCC)C>[C:1]([NH:8][C:9]([CH3:13])([CH3:12])[CH:10]=[O:11])([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Komponenten

6

Edukt 3

HCID 14798Sodium HydroxideHCID 159087TriacetoxyperiodinaneHCID 14578673tert-butyl N-(1-hydroxy-2-methylpropan-2-yl)carbamate

Produkt 1

HCID 14578674tert-butyl N-(2-methyl-1-oxopropan-2-yl)carbamateAusbeute 87,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

The resulting N-BOC-2-amino-2-methyl-1-propanol (3.69 g, 19.5 mmol) was dissolved in methylene chloride (74 ml) and added to a stirred suspension of Dess-Martin periodinane (10.75 g, 25.35 mmol; Aldrich Chemical Company, Milwaukee, Wis.) in methylene chloride (89 ml). After stirring for 20 minutes under nitrogen, the reaction mixture was diluted with diethyl ether (370 ml), poured into sodium hydroxide (148 ml, 1.3M) and stirred for ten minutes. The aqueous sodium hydroxide layer was separated and discarded. The remaining organic solution was washed successively with sodium hydroxide (148 ml, 1.3M) and H2O (185 ml). After drying over magnesium sulfate, the solvent was removed in vacuo to yield 3.21 grams of N-BOC-2-amino-2-methyl-1-propanal.

Aufarbeitung

  1. stirringstirred for ten minutes
  2. customThe aqueous sodium hydroxide layer was separated
  3. washThe remaining organic solution was washed successively with sodium hydroxide (148 ml, 1.3M) and H2O (185 ml)
  4. dry with materialAfter drying over magnesium sulfate
  5. customthe solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-9ae2160c95854c49add8e88e86c3dc61
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05248791

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