Ethyl Acetate → tert-butyl (2S,4R)-4-((tert-butyldimethylsilyl)oxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

HRID 406493

反応式

HRID 406493 の反応式
[Si:1]([O:8][C@H:9]1[CH2:13][N:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C@H:11]([C:21](OC)=[O:22])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[BH4-].[Li+].C(OCC)(=O)C>C1COCC1>[Si:1]([O:8][C@H:9]1[CH2:13][N:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C@H:11]([CH2:21][OH:22])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

参加物

5

反応物 3

HCID 8857Ethyl AcetateHCID 4148881Lithium borohydrideHCID 10618477(2S,4R)-1-tert-Butyl 2-methyl 4-((tert-butyldimethylsilyl)oxy)pyrrolidine-1,2-dicarboxylate

生成物 1

HCID 11078078tert-butyl (2S,4R)-4-((tert-butyldimethylsilyl)oxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylate収率 97.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of (2S,4R)-1-tert-butyl 2-methyl 4-(tert-butyldimethylsilyloxy)pyrrolidine-1,2-dicarboxylate (5.34 g, 14.8 mmol) in THF (20 mL) was cooled to 0° C. and lithium borohydride (0.485 g, 22.2 mmol) in THF (10 mL) was added dropwise. The mixture was stirred for about 16 hours while the ice-salt bath gradually melted. Ethyl acetate (30 mL) was added followed by the addition of ice. The organic portion was separated and quenched by a dropwise addition of 1N aqueous phosphoric acid. The organic portion was separated and washed with water (120 mL), saturated sodium bicarbonate solution (2×120 mL), and brine (100 mL) and dried over magnesium sulfate. The filtrate was concentrated under reduced pressure to yield (2S,4R)-tert-butyl 4-(tert-butyldimethylsilyloxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylate (4.8 g, 14.4 mmol) as a colorless oil. RP-HPLC (Table 1, Method f) Rt 6.25 min; m/z: (M−H)− 390.

後処理

  1. additionfollowed by the addition of ice
  2. customThe organic portion was separated
  3. customquenched by a dropwise addition of 1N aqueous phosphoric acid
  4. customThe organic portion was separated
  5. washwashed with water (120 mL), saturated sodium bicarbonate solution (2×120 mL), and brine (100 mL)
  6. dry with materialdried over magnesium sulfate
  7. concentrationThe filtrate was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-20ac201969ed4b9c8df45b5dcad01bb9
出典データセット
uspto-grants-2014_06
特許番号
US08754107B2

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