Dimethylamine → tert-butyl (2S,4S)-2-(dimethylcarbamoyl)-4-hydroxypyrrolidine-1-carboxylate

HRID 490120

반응식

HRID 490120 반응식
Cl.[CH2:2]([N:4]=[C:5]=NCCCN(C)C)C.[C:13]([O:17][C:18]([N:20]1[CH2:27][C@@H:26]([OH:28])[CH2:25][C@H:21]1[C:22](O)=[O:23])=[O:19])([CH3:16])([CH3:15])[CH3:14].O.ON1C2C=CC=CC=2N=N1.CNC.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.CCCCCC.C(Cl)(Cl)Cl.O1CCCC1>[CH3:2][N:4]([CH3:5])[C:22]([C@@H:21]1[CH2:25][C@H:26]([OH:28])[CH2:27][N:20]1[C:18]([O:17][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:19])=[O:23]

참가 물질

9

반응물 5

HCID 674DimethylamineHCID 11430Potassium CarbonateHCID 688614(2S,4S)-1-(tert-butoxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

생성물 1

HCID 67430109tert-butyl (2S,4S)-2-(dimethylcarbamoyl)-4-hydroxypyrrolidine-1-carboxylate수율 77.5%

시약·촉매·용매 3

HCID 6212Chloroform용매HCID 8028Tetrahydrofuran용매HCID 21226206Ethyl acetate hexane용매

실험 절차

9.95 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride was added under ice cooling to a 100 mL tetrahydrofuran solution of 10.0 g of (4S)-1-(tert-butoxycarbonyl)-4-hydroxy-L-proline and 8.77 g of 1-hydroxybenzotriazole monohydrate, and the reaction mixture was stirred for 30 minutes at the same temperature. 15.6 g of a 50% dimethylamine aqueous solution was than added to the reaction solution, after which the reaction mixture was stirred for 1 hour at room temperature. 100 mL of chloroform and 50 mL of a 5% potassium carbonate aqueous solution were added to the reaction solution, liquid separation was performed, the aqueous layer was extracted with chloroform (30 mL×2), and the combined organic layer was washed with 30 mL of saturated brine and dried with magnesium sulfate, after which the drying agent was filtered off and the solvent was distilled off under reduced pressure. The residue thus obtained was subjected to column chromatography (silica gel 60, mobile phase: ethyl acetate/n-hexane=1/1 to 10/0; v/v) to obtain 8.66 g of the titled compound (colorless solid).

후처리

  1. additionthan added to the reaction solution
  2. stirringafter which the reaction mixture was stirred for 1 hour at room temperature
  3. extractionthe aqueous layer was extracted with chloroform (30 mL×2)
  4. washthe combined organic layer was washed with 30 mL of saturated brine
  5. dry with materialdried with magnesium sulfate
  6. filtrationafter which the drying agent was filtered off
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue thus obtained

출처 및 근거

ORD 기록
ord-fa0451fe978d46ea9a63b39814c5ade1
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07528124B2

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