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

HRID 870812ノート

反応式

HRID 870812 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

反応条件

温度
-40 °C

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 stirred 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-49b81a273a924b3585eedc0a0a3ea24b
出典データセット
uspto-grants-2015_03
特許番号
US08969570B2

反応ノート

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