Reaktion #160098

Reaktionsgleichung

Methyl iodide

tert-butyl 8-tert-butyl-10-(hydroxymethyl)-11-oxa-3,8-diazaspiro[5.5]undecane-3-carboxylate

sodium hydride

→

tert-butyl 8-tert-butyl-10-(methoxymethyl)-11-oxa-3,8-diazaspiro[5.5]undecane-3-carboxylate

Ausbeute 98.0%

Lösungsmittel

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe reaction mixture stirred for 20 min
2. 2
   SonstigeThe reaction was quenched with saturated aqueous NH4Cl
3. 3
   Extraktionextracted with ethyl acetate (2×25 mL)
4. 4
   TrocknenThe combined organic layers were dried over Na2SO4
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated

Vorschrift

To a solution of tert-butyl 8-tert-butyl-10-(hydroxymethyl)-11-oxa-3,8-diazaspiro[5.5]undecane-3-carboxylate (720 mg, 2.10 mmol) in N,N-dimethylformamide (7.0 mL) was added sodium hydride (588 mg, 14.7 mmol) and the reaction stirred for 10 min. Methyl iodide (916 μL, 14.7 mmol) was added and the reaction mixture stirred for 20 min. The reaction was quenched with saturated aqueous NH4Cl and extracted with ethyl acetate (2×25 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated to provide tert-butyl 8-tert-butyl-10-(methoxymethyl)-11-oxa-3,8-diazaspiro[5.5]undecane-3-carboxylate (732 mg, 2.05 mmol, 98%). ESI-MS m/z calc. 356.3. Found 357.3 (M+1)+; Retention time: 0.97 minutes (3 min run).

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