反応 #1123865

反応方程式

(R)-3-(benzyloxy)-2-(tert-butoxycarbonylamino)propanoic acid

T3P

DIPEA

(4R,5S)-2-Methyl-4-phenyl-2,7-diazaspiro[4.5]decan-1-one

(4S,5R)-2-Methyl-4-phenyl-2,7-diazaspiro[4.5]decan-1-one

Intermediate 1A

(4S,5R)-2-Methyl-4-phenyl-2,7-diazaspiro[4.5]decan-1-one

→

title compound

tert-butyl (2R)-3-(benzyloxy)-1-(2-methyl-1-oxo-4-phenyl-2,7-diazaspiro[4.5]decan-7-yl)-1-oxopropan-2-ylcarbamate

溶媒

HCl

MeCN

反応条件

後処理

1. 1
   workup.ADDITIONwas added portionwise
2. 2
   workup.STIRRINGThe reaction mixture was stirred for 20 hours at room temperature
3. 3
   抽出extracted with DCM (20 mL)
4. 4
   抽出The aqueous phase was further extracted with DCM (3×20 mL)
5. 5
   洗浄The combined organic portions were washed with a saturated solution of sodium bicarbonate (20 mL), water (20 mL)
6. 6
   乾燥dried (MgSO4)
7. 7
   濃縮concentrated in vacuo

実験手順

A mixture comprising (R)-3-(benzyloxy)-2-(tert-butoxycarbonylamino)propanoic acid (Sigma-Aldrich) (1.052 g, 3.56 mmol) and ®T3P (50% in EtOAc) (4.16 ml, 7.12 mmol) in MeCN (20 mL) was treated dropwise with DIPEA (2.488 ml, 14.25 mmol). The resulting solution was stirred at room temperature for 30 minutes, then a racemic mixture of (4R,5S)-2-Methyl-4-phenyl-2,7-diazaspiro[4.5]decan-1-one and (4S,5R)-2-Methyl-4-phenyl-2,7-diazaspiro[4.5]decan-1-one (Intermediate 1A) (1 g, 3.56 mmol) was added portionwise. The reaction mixture was stirred for 20 hours at room temperature. The reaction mixture was diluted with 0.1M HCl (20 mL) and extracted with DCM (20 mL). The aqueous phase was further extracted with DCM (3×20 mL). The combined organic portions were washed with a saturated solution of sodium bicarbonate (20 mL), water (20 mL), dried (MgSO4), and concentrated in vacuo to afford the title compound. No purification was performed on the title compound.

出典