Reaktion #1349033

Reaktionsgleichung

sodium hydrogencarbonate

Sodium triacetoxyborohydride

(3S,5S)-3-allyl-5-formyl-morpholine-4-carboxylic acid tert-butyl ester

L-alanine methyl ester hydrochloride

benzyl chloroformate

→

title compound

Ausbeute 100.0%

(3S,5R)-3-Allyl-5-{[benzyloxycarbonyl-((S)-1-methoxycarbonyl-ethyl)-amino]-methyl}-morpholine-4-carboxylic acid tert-butyl ester

Ausbeute 100.0%

Lösungsmittel

water

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeafter 16 h the reaction mixture was partitioned between sat. aq. sodium hydrogencarbonate solution and DCM
2. 2
   WaschenThe organic layer was washed with brine
3. 3
   Trocknendried over magnesium sulfate
4. 4
   Filtrationfiltered
5. 5
   Sonstigeevaporated
6. 6
   SonstigeThe ice bath was removed
7. 7
   Sonstigeafter 1 h the reaction mixture was partitioned between EtOAc and water
8. 8
   TrocknenThe organic layer was dried over magnesium sulfate
9. 9
   Filtrationfiltered
10. 10
    Sonstigeevaporated

Vorschrift

Sodium triacetoxyborohydride (628 mg, 2.96 mmol) were added at 0° C. to a solution of (3S,5S)-3-allyl-5-formyl-morpholine-4-carboxylic acid tert-butyl ester (608 mg, 2.12 mmol) and L-alanine methyl ester hydrochloride (295 mg, 2.12 mmol) in DCM (8 mL), then after 16 h the reaction mixture was partitioned between sat. aq. sodium hydrogencarbonate solution and DCM. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and evaporated. The residue [(3S,5R)-3-allyl-5-[((S)-1-methoxycarbonyl-ethylamino)-methyl]-morpholine-4-carboxylic acid tert-butyl ester, MS: 343.3 (M+H)|] was taken up in acetone (3.5 mL) and water (3.5 mL), then after addition of sodium hydrogencarbonate (355 mg, 4.23 mmol), the reaction mixture was cooled to 0° C. and treated with benzyl chloroformate (380 mg, 2.12 mmol). The ice bath was removed, then after 1 h the reaction mixture was partitioned between EtOAc and water. The organic layer was dried over magnesium sulfate, filtered, and evaporated to afford the title compound (1.01 g, 100%). Light yellow oil, MS: 477.3 (M+H)+.

Quelle