Lithiumtriethylborohydride → 1,1-Dimethylethyl (2R,3S)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-(hydroxymethyl)-1-pyrrolidinecarboxylate

HRID 132684ノート

反応式

HRID 132684 の反応式
C[O:2][C:3](=O)[C@@H:4]1[C@@H:8]([O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11])[CH2:7][CH2:6][N:5]1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].C([BH-](CC)CC)C.[Li+]>C1COCC1>[C:20]([O:19][C:17]([N:5]1[CH2:6][CH2:7][C@H:8]([O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11])[C@H:4]1[CH2:3][OH:2])=[O:18])([CH3:23])([CH3:22])[CH3:21]

参加物

4

反応物 2

HCID 23664628LithiumtriethylborohydrideHCID 58841066Methyl (2S,3S)-1-Boc-3-[(tert-butyldimethylsilyl)oxy]pyrrolidine-2-carboxylate

生成物 1

HCID 109256021,1-Dimethylethyl (2R,3S)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-(hydroxymethyl)-1-pyrrolidinecarboxylate収率 83%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of compound 1H (4.3 g, 12 mmol) in THF (75 mL) at −78° C. under nitrogen was added dropwise 1.0 M lithium triethylborohydride in THF (60 mL, 60 mmol). The reaction was allowed to warm to rt and stirred for 4 h. The reaction was quenched by pouring over ice (150 g) and stirring for 30 min. The product was extracted into EtOAc and washed with saturated aqueous NaHCO3. The organics were dried over MgSO4, filtered and concentrated. Purification by flash chromatography (silica gel, 0-15% EtOAc in hexanes) provided the title compound (3.3 g).

後処理

  1. customThe reaction was quenched
  2. additionby pouring over ice (150 g)
  3. stirringstirring for 30 min
  4. extractionThe product was extracted into EtOAc
  5. washwashed with saturated aqueous NaHCO3
  6. dry with materialThe organics were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by flash chromatography (silica gel, 0-15% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-3835becebbcc42bc819103bf62072944
出典データセット
uspto-grants-2008_06
特許番号
US07388027B2

反応ノート

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