Hydrochloric Acid → (2S,4R)-Tert-butyl 2-(hydroxymethyl)-4-(methylsulfonyloxy)pyrrolidine-1-carboxylate

HRID 1941616ノート

反応式

HRID 1941616 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][S:14]([CH3:17])(=[O:16])=[O:15])[CH2:10][C@H:9]1[C:18](OC(OCC)=O)=[O:19])=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].Cl>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][S:14]([CH3:17])(=[O:15])=[O:16])[CH2:10][C@H:9]1[CH2:18][OH:19])=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 22880732HCID 22880732、化合物

生成物 1

HCID 10589967(2S,4R)-Tert-butyl 2-(hydroxymethyl)-4-(methylsulfonyloxy)pyrrolidine-1-carboxylate収率 94%

試薬・触媒・溶媒 2

HCID 74236Tetrabutylammonium Bromide触媒HCID 962Water溶媒

反応条件

温度
-40 °C

実験手順

To the resulting reaction mixture containing (2S,4R)-1-t-butoxycarbonyl-2-ethoxycarbonyloxycarbonyl-4-methane sulfonyloxypyrrolidine obtained in Step D-3 cooling at -40° C., tetra-n-butylammonium bromide (11.8 g: 0.0365 mole) and a solution of sodium borohydride (52.5 g: 1.35 mole) in water (55 ml) are added. The mixture is allowed to warm to -10° C. and stirred for 1 hour. The aqueous layer is acidified with dilute hydrochloric acid to pH 3. The organic layer is taken, successively washed with aqueous sodium hydrogen carbonate and water, dried over magnesium sulfate, and concentrated under reduced pressure. The residue is recrystallized from a toluene-hexane mixture to give (2S,4R)-1-t-butoxycarbonyl-4-methanesulfonyloxypyrrolidine-2-methanol (101.3 g). Yield: 94%. Colorless crystals. mp. 95° to 96° C.

後処理

  1. customTo the resulting reaction mixture
  2. temperatureto warm to -10° C.
  3. washsuccessively washed with aqueous sodium hydrogen carbonate and water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is recrystallized from a toluene-hexane mixture

出典と根拠

ORDレコード
ord-446c1538a699481cb678e27f38eea041
出典データセット
uspto-grants-1997_12
特許番号
US05703243

反応ノート

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