Sodium Azide → (3R,5S)-5-(azidomethyl)-3-(3-chloropropyl)pyrrolidin-2-one

HRID 2039952ノート

反応式

HRID 2039952 の反応式
[N+](C1C=CC(S(O[CH2:14][C@@H:15]2[CH2:19][C@@H:18]([CH2:20][CH2:21][CH2:22][Cl:23])[C:17](=[O:24])[NH:16]2)(=O)=O)=CC=1)([O-])=O.[N-:25]=[N+:26]=[N-:27].[Na+].[N-]=[N+]=[N-]>CN(C=O)C>[N:25]([CH2:14][C@H:15]1[NH:16][C:17](=[O:24])[C@H:18]([CH2:20][CH2:21][CH2:22][Cl:23])[CH2:19]1)=[N+:26]=[N-:27]

参加物

5

反応物 3

HCID 33557Sodium AzideHCID 33558AzideHCID 58011487((2S,4R)-4-(3-chloropropyl)-5-oxopyrrolidin-2-yl)methyl 4-nitrobenzenesulfonate

生成物 1

HCID 86637155(3R,5S)-5-(azidomethyl)-3-(3-chloropropyl)pyrrolidin-2-one

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

The ((2S,4R)-4-(3-chloropropyl)-5-oxopyrrolidin-2-yl)methyl 4-nitrobenzenesulfonate (18.05 g, 45.2 mmol) and NaN3 (3.23 g, 49.7 mmol, 1.1 equiv) were stirred in 100 mL of DMF for 19 h. After this time a white solid had formed and LC/MS analysis showed formation of the desired azide. The DMF was removed in vacuo and the residue partitioned between EtOAc/H2O (100+100 mL). The mixture was transferred to a separatory funnel and the layers separated. The aqueous layer was extracted with 100 mL additional EtOAc and the combined organic extracts washed with brine, dried over Na2SO4, filtered and evaporated. The (3R,5S)-5-(azidomethyl)-3-(3-chloropropyl)pyrrolidin-2-one was isolated as a pale yellow syrup (9.08 g, 94% yield).

後処理

  1. customAfter this time a white solid had formed
  2. customThe DMF was removed in vacuo
  3. customthe residue partitioned between EtOAc/H2O (100+100 mL)
  4. customThe mixture was transferred to a separatory funnel
  5. customthe layers separated
  6. extractionThe aqueous layer was extracted with 100 mL additional EtOAc
  7. washthe combined organic extracts washed with brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. customevaporated

出典と根拠

ORDレコード
ord-00c371c89e4f46b69828f92f9a0836f4
出典データセット
uspto-grants-2013_11
特許番号
US08580823B2

反応ノート

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