Hydrochloric Acid → 2-Methyl-4-(4-nitro-benzoyloxy)-pyrrolidine-1-carboxylic Acid T-butyl Ester

HRID 1071505ノート

反応式

HRID 1071505 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([OH:13])[CH2:10][CH:9]1[CH3:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N+:34]([C:37]1[CH:45]=[CH:44][C:40]([C:41](O)=[O:42])=[CH:39][CH:38]=1)([O-:36])=[O:35].CCOC(/N=N/C(OCC)=O)=O.Cl>C1COCC1.CCCCCC.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([O:13][C:41](=[O:42])[C:40]2[CH:39]=[CH:38][C:37]([N+:34]([O-:36])=[O:35])=[CH:45][CH:44]=2)[CH2:10][CH:9]1[CH3:14])=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 61084-Nitrobenzoic AcidHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 14117009tert-Butyl 4-hydroxy-2-methylpyrrolidine-1-carboxylate

生成物 1

HCID 685656492-Methyl-4-(4-nitro-benzoyloxy)-pyrrolidine-1-carboxylic Acid T-butyl Ester

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 21226206Ethyl acetate hexane溶媒

反応条件

温度
0 °C

実験手順

The 4-hydroxy-2-methyl-pyrrolidine-1-carboxylic acid t-butyl ester (300.00 mg, 1.49 mmol) and triphenyl phosphine (512.54, 1.95 mmol) were dissolved in anhydrous THF and added to a mixture of para-nitrobenzoic acid (249.00 mg, 1.49 mmol) and DEAD (268.00 mg, 1.54 mmol, 0.24 mL) in anhydrous THF at 0° C. under argon. The mixture was stirred for 1 h at 0° C. After 1 h the TLC indicated no starting material remained and the reaction mixture was poured into a 1N HCl solution and the aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed with water and brine then dried over MgSO4. The solution was filtered and the solvent removed under reduced pressure. The product was isolated by flash chromatography. (2:1 hexane-ethyl acetate) Yield 391.54 mg.

後処理

  1. waitAfter 1 h the TLC indicated
  2. extractionthe aqueous layer was extracted three times with ethyl acetate
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialthen dried over MgSO4
  5. filtrationThe solution was filtered
  6. customthe solvent removed under reduced pressure
  7. customThe product was isolated by flash chromatography

出典と根拠

ORDレコード
ord-23021509e741490fbf90d106cf552d1c
出典データセット
uspto-grants-2005_06
特許番号
US06906067B2

反応ノート

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