HCID 688299、化合物 → HCID 86696675、化合物

HRID 2365823ノート

反応式

HRID 2365823 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Mg]Br)=[CH:4][C:3]=1[F:10].CON(C)[C:14]([C@H:16]1[CH2:20][CH2:19][CH2:18][N:17]1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[O:15]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:14]([C@H:16]2[CH2:20][CH2:19][CH2:18][N:17]2[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[O:15])=[CH:4][C:3]=1[F:10]

参加物

4

反応物 2

HCID 688299HCID 688299、化合物HCID 178505943HCID 178505943、化合物

生成物 1

HCID 86696675HCID 86696675、化合物収率 61%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

0.5M (4-Chloro-3-fluorophenyl)magnesium bromide (22.5 mL, 11.2 mmol) as a solution in THF was added dropwise to a cold (0° C.) solution of (R)-tert-butyl 2-(methoxy(methyl)carbamoyl)pyrrolidine-1-carboxylate (1.45 g, 5.61 mmol) in THF (25 mL) under N2, and the reaction was allowed to warm up to room temperature overnight. The next morning, the mixture was placed in an ice bath and carefully quenched with ice. The reaction mixture was concentrated. The residue was treated for 1 hour with a solution of 30% sodium potassium and then extracted with ethyl acetate (2×). The organic layer was dried, filtered and concentrated. The crude product was purified via column chromatography, eluting with hexanes/ethyl acetate (5:1) to give (R)-tert-butyl 2-(4-chloro-3-fluorobenzoyl)pyrrolidine-1-carboxylate (1.12 g, 61%). m/z (APCI-pos) (M+1)-Boc=228.1, 230.1.

後処理

  1. customThe next morning, the mixture was placed in an ice bath
  2. customcarefully quenched with ice
  3. concentrationThe reaction mixture was concentrated
  4. additionThe residue was treated for 1 hour with a solution of 30% sodium potassium
  5. extractionextracted with ethyl acetate (2×)
  6. customThe organic layer was dried
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was purified via column chromatography
  10. washeluting with hexanes/ethyl acetate (5:1)

出典と根拠

ORDレコード
ord-d8d905e11af144328f5c3623451db56b
出典データセット
uspto-grants-2014_04
特許番号
US08697715B2

反応ノート

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