Reaktion #44768

Reaktionsgleichung

1-Boc-2-aminomethylpiperidine

methyl 4-formylbenzoate

acetic acid

sodium triacetoxyborohydride

→

1,1-dimethylethyl 2-((4-(methoxycarbonyl)phenylmethylamino)methyl)-1-piperidinecarboxylate

Ausbeute 96.6%

Lösungsmittel

dichloroethane

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwere added sequentially
2. 2
   Extraktionextracted with methylene chloride (2×)
3. 3
   TrocknenThe organic phase was dried over sodium sulfate
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated
6. 6
   SonstigePurification on silica gel using a gradient of ethyl acetate in hexane

Vorschrift

A solution of 1-Boc-2-aminomethylpiperidine (429 mg, 2 mmol) and methyl 4-formylbenzoate (329 mg, 2 mmol) in dichloroethane (10 mL) was stirred as acetic acid (180 mg, 3 mmol) and sodium triacetoxyborohydride (487 mg, 2.3 mmol) were added sequentially. The reaction was stirred at ambient temperature for 17 hours. The reaction was poured into water and extracted with methylene chloride (2×). The organic phase was dried over sodium sulfate, filtered, and concentrated. Purification on silica gel using a gradient of ethyl acetate in hexane gave 0.7 g of 1,1-dimethylethyl 2-((4-(methoxycarbonyl)phenylmethylamino)methyl)-1-piperidinecarboxylate.

Quelle