Methanol → tert-Butyl 3-(hydroxymethyl)azetidine-1-carboxylate

HRID 1627562Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1627562
[N:1]1([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4][CH:3]([C:5](OC)=[O:6])[CH2:2]1.CO.[Li+].[BH4-].O.O.O.O.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C1COCC1.CCOC(C)=O>[OH:6][CH2:5][CH:3]1[CH2:4][N:1]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:2]1

Komponenten

7

Edukt 4

HCID 887MethanolHCID 2724148Sodium potassium tartrate tetrahydrateHCID 4148881Lithium borohydrideHCID 446076271-tert-Butyl 3-methyl azetidine-1,3-dicarboxylate

Produkt 1

HCID 10583745tert-Butyl 3-(hydroxymethyl)azetidine-1-carboxylateAusbeute 73,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

1-tert-butyl 3-methyl azetidine-1,3-dicarboxylate (1055 mg, 4.90 mmol) was dissolved in THF (17 mL) and then cooled to 0° C. MeOH (0.397 mL, 9.80 mmol) and LiBH4 (14.7 mmol) were added sequentially. The reaction was warmed to room temperature over 3 h. Then 10% aqueous potassium sodium tartrate tetrahydrate (Rochelle's Salt) (30 mL) and EtOAc (30 mL) were added and the solution stirred at room temperature over 30 minutes. The organic layer was separated and then dried (Na2SO4) and concentrated to afford 674 mg of t-butyl 3-(hydroxymethyl)azetidine-1-carboxylate (1-3) as a crude product (clear oil). The product was used directly in the next step without purification.

Aufarbeitung

  1. temperatureThe reaction was warmed to room temperature over 3 h
  2. customThe organic layer was separated
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-95f7646c3828436ca9bec9e8800a72bb
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785632B2

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