Sodium Bicarbonate → tert-butyl (4S)-4-(3-fluoropropyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

HRID 2401281ノート

反応式

HRID 2401281 の反応式
O[CH2:2][CH2:3][CH2:4][C@H:5]1[CH2:9][O:8][C:7]([CH3:11])([CH3:10])[N:6]1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].COCCN(S(F)(F)[F:29])CCOC.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[F:29][CH2:2][CH2:3][CH2:4][C@H:5]1[CH2:9][O:8][C:7]([CH3:11])([CH3:10])[N:6]1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13]

参加物

5

反応物 3

HCID 516892Sodium BicarbonateHCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 10879805Tert-butyl (4S)-4-(3-hydroxypropyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

生成物 1

HCID 86705185tert-butyl (4S)-4-(3-fluoropropyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

A solution of tert-butyl (4S)-4-(3-hydroxypropyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (3.05 g) in chloroform (40 mL) was cooled in a dry ice-acetone bath, bis(2-methoxyethyl)aminosulfur trifluoride (2.77 mL) was added thereto, and the mixture was stirred at room temperature for 3 hr. Saturated aqueous sodium hydrogen carbonate solution was added thereto, and the organic layer was washed with water and brine, followed by drying with anhydrous sodium sulfate. After the desiccant was filtered off, the filtrate was concentrated under reduced pressure, and the residue was purified by column chromatography (silica gel cartridge, hexane/ethyl acetate=10:1-2:1) to afford tert-butyl (4S)-4-(3-fluoropropyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (900 mg).

後処理

  1. washthe organic layer was washed with water and brine
  2. dry with materialby drying with anhydrous sodium sulfate
  3. filtrationAfter the desiccant was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customthe residue was purified by column chromatography (silica gel cartridge, hexane/ethyl acetate=10:1-2:1)

出典と根拠

ORDレコード
ord-64ad1954f1454d219e50008c89813cd9
出典データセット
uspto-grants-2014_08
特許番号
US08796272B2

反応ノート

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