tert-Butyl 4-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate → Tert-butyl 4-(4-methoxy-3-methylbenzoyl)piperidine-1-carboxylate

HRID 1752236ノート

反応式

HRID 1752236 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=[O:19])N(OC)C)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([Mg]Br)=[CH:24][C:23]=1[CH3:30]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14](=[O:19])[C:25]2[CH:26]=[CH:27][C:22]([O:21][CH3:20])=[C:23]([CH3:30])[CH:24]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

参加物

4

反応物 2

HCID 11065582tert-Butyl 4-(methoxy(methyl)carbamoyl)piperidine-1-carboxylateHCID 178491913HCID 178491913、化合物

生成物 1

HCID 71212195Tert-butyl 4-(4-methoxy-3-methylbenzoyl)piperidine-1-carboxylate収率 99%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 4-(methoxy-methyl-carbamoyl)-piperidine-1-carboxylic acid tert-butyl ester (5.0 g, 18.36 mmol) in 50 mL dry THF at ambient temperature was added (4-methoxy-3-methylphenyl)magnesium bromide (55.1 mL, 0.5 M) was added dropwise under N2, the reaction mixture was stirred at the same temperature for 16 hours. The reaction was quenched with saturated sodium sulfate solution (10 mL) and partitioned between brine (150 mL) and 10% isopropyl alcohol/chloroform (200 mL), and the organic layer was removed to yield the crude product. Purification by flash chromatography (silica: 5-35% ethyl acetate/pentane) gave the title compound as a white solid (6.4 g, 19.21 mmol, >99% yield). HPLC (Novapak 150×3.9 mm C-18 column: mobile phase: 10-90% acetonitrile/water with 0.1% TFA, at 2 mL/min over 2 min.) retention time=4.131 min.

後処理

  1. additionwas added dropwise under N2
  2. customThe reaction was quenched with saturated sodium sulfate solution (10 mL)
  3. custompartitioned between brine (150 mL) and 10% isopropyl alcohol/chloroform (200 mL)
  4. customthe organic layer was removed
  5. customto yield the crude product
  6. customPurification by flash chromatography (silica: 5-35% ethyl acetate/pentane)

出典と根拠

ORDレコード
ord-4fed1aa347e04fb6b9d445d76dc1fc86
出典データセット
uspto-grants-2015_10
特許番号
US09163003B2

反応ノート

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