Methyl iodide → tert-butyl N-[(2S)-2-methoxypropyl]carbamate

HRID 2092922ノート

反応式

HRID 2092922 の反応式
[C:1]([O:5][C:6](=[O:12])[NH:7][CH2:8][C@@H:9]([OH:11])[CH3:10])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:15]I>O1CCCC1>[CH3:15][O:11][C@@H:9]([CH3:10])[CH2:8][NH:7][C:6](=[O:12])[O:5][C:1]([CH3:2])([CH3:4])[CH3:3]

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 11789722N-Boc-(S)-1-amino-2-propanol

生成物 1

HCID 86643351tert-butyl N-[(2S)-2-methoxypropyl]carbamate収率 94%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Cool a solution of tert-butyl[(2S)-2-hydroxypropyl]carbamate (870 g, 4.96 mol) in tetrahydrofuran (10 L) to 5° C. Add sodium hydride (60% dispersion, 248 g, 6.21 mol, 1.25 eq.) in portions over 8 minutes. Stir the reaction at 5° C. for 30 minutes. Add methyl iodide (387 mL, 6.21 mol, 1.25 eq.) dropwise over 5 minutes and allow the reaction to proceed at 5-10° C. for 45 minutes. Quench the reaction with water (1 L) and extract with ethyl acetate (4 L). Obtain the organic layer and concentrate it in vacuo to obtain a residue. Co-evaporate the residue with toluene (2×1 L), dilute with dichloromethane (2 L) and filter. Rinse remaining solid with additional dichloromethane (500 mL). Concentrate the combined dichloromethane liquid filtrate in vacuo to obtain a crude intermediate of tert-butyl N-[(2S)-2-methoxypropyl]carbamate (880 g, 94%).

後処理

  1. customthe reaction at 5° C. for 30 minutes
  2. customthe reaction
  3. customQuench
  4. customthe reaction with water (1 L)
  5. extractionextract with ethyl acetate (4 L)
  6. customObtain the organic layer
  7. concentrationconcentrate it in vacuo
  8. customto obtain a residue
  9. customCo-evaporate the residue with toluene (2×1 L)
  10. additiondilute with dichloromethane (2 L)
  11. filtrationfilter
  12. washRinse
  13. concentrationConcentrate the combined dichloromethane liquid filtrate in vacuo

出典と根拠

ORDレコード
ord-c439ef1efb6b4aafafd1b50c505d9732
出典データセット
uspto-grants-2013_05
特許番号
US08440829B2

反応ノート

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