Aluminium lithium hydride → tert-butyl(2R,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-2-(hydroxymethyl)piperidine-1-carboxylate

HRID 255356ノート

反応式

HRID 255356 の反応式
[Si:1]([O:8][C@H:9]1[CH2:14][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C@@H:12]([C:22](OCC)=[O:23])[CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[Si:1]([O:8][C@H:9]1[CH2:14][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C@@H:12]([CH2:22][OH:23])[CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 691850781-tert-butyl 2-ethyl (2R,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}piperidine-1,2-dicarboxylate2 回

生成物 1

HCID 66773985tert-butyl(2R,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-2-(hydroxymethyl)piperidine-1-carboxylate収率 88.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 1-tert-butyl 2-ethyl (2R,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}piperidine-1,2-dicarboxylate (Intermediate 191, 9.99 g) in THF (100 mL) was added lithium aluminium hydride (1M in THF, 30 mL). After 2 hours, the reaction was quenched with ethyl acetate, washed with 1 N HCl, NaHCO3 and brine solutions, dried (Na2SO4), filtered and concentrated yielding 7.9 g of product.

後処理

  1. customthe reaction was quenched with ethyl acetate
  2. washwashed with 1 N HCl, NaHCO3 and brine solutions
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-b4bf4206bedb408eb41048a9f91ff4a1
出典データセット
uspto-grants-2011_01
特許番号
US07875715B2

反応ノート

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