Benzyl 4-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate → Benzyl 4-acetylpiperidine-1-carboxylate

HRID 1351550ノート

反応式

HRID 1351550 の反応式
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([C:17](=[O:22])N(OC)C)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:23][Mg]Br>C1COCC1.CCOCC>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13][CH:14]([C:17](=[O:22])[CH3:23])[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 2

HCID 22574154Benzyl 4-(methoxy(methyl)carbamoyl)piperidine-1-carboxylateHCID 178418573HCID 178418573、化合物

生成物 1

HCID 19065050Benzyl 4-acetylpiperidine-1-carboxylate

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a solution of 5 g of 4-(N-methoxy-N-methyl-carbamoyl)-piperidine-1-carboxylic acid benzyl ester (S. Nahm and S. W. Weinreb, Tetrahedron Letters, 22:3815–3818(1981)) in 50 mL of anhydrous THF cooled to 0° C., was added dropwise 6 mL of 3M methylmagnesium bromide in ether over 10 minutes. After stirring for 1 h at 0° C., the resulting mixture was quenched with 50 mL of 1N HCl and extracted with 3×50 mL of ether. The combined extracts were dried over magnesium sulfate and concentrated to dryness under reduced pressure. Drying under vacuum gave 4-Acetyl-piperidine-1-carboxylic acid benzyl ester as a white solid:

後処理

  1. customthe resulting mixture was quenched with 50 mL of 1N HCl
  2. extractionextracted with 3×50 mL of ether
  3. dry with materialThe combined extracts were dried over magnesium sulfate
  4. concentrationconcentrated to dryness under reduced pressure
  5. customDrying under vacuum

出典と根拠

ORDレコード
ord-00c25f69a5a9475cae5d6e5ff53cfea5
出典データセット
uspto-grants-2007_05
特許番号
US07217716B2

反応ノート

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