Sodium borohydride → (2S,5S)-1-tert-butyl 2-ethyl 5-hydroxypiperidine-1,2-dicarboxylate

HRID 1406845ノート

反応式

HRID 1406845 の反応式
[BH4-].[Na+].[O:3]=[C:4]1[CH2:9][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@H:7]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:6][CH2:5]1>CCO>[OH:3][C@@H:4]1[CH2:9][N:8]([C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])[C@H:7]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:6][CH2:5]1

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 70701166(S)-1-tert-butyl 2-ethyl 5-oxopiperidine-1,2-dicarboxylate

生成物 1

HCID 86700663(2S,5S)-1-tert-butyl 2-ethyl 5-hydroxypiperidine-1,2-dicarboxylate収率 81.5%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

NaBH4 (36 g, 1.0 mol) was added in portions to a solution of (S)-1-tert-butyl 2-ethyl 5-oxopiperidine-1,2-dicarboxylate (250 g, 0.92 mol) in EtOH (1500 mL) at −40° C. The reaction mixture was then stiffed at −40° C. for 0.5 hr then quenched with 10% HOAc solution. After diluting with water, the mixture was extracted with DCM three times. The combined organic layer was concentrated in vacuum and purified by silica gel column chromatography (1:1 petroleum ether/EtOAc) to afford (2S,5S)-1-tert-butyl 2-ethyl 5-hydroxypiperidine-1,2-dicarboxylate (205 g, 80%) as a yellow oil.

後処理

  1. customthen quenched with 10% HOAc solution
  2. additionAfter diluting with water
  3. extractionthe mixture was extracted with DCM three times
  4. concentrationThe combined organic layer was concentrated in vacuum
  5. custompurified by silica gel column chromatography (1:1 petroleum ether/EtOAc)

出典と根拠

ORDレコード
ord-e343bdaf23d742e3afede27aeed9955f
出典データセット
uspto-grants-2014_12
特許番号
US08916709B2

反応ノート

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