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

HRID 870812노트

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HRID 870812 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
-40 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-49b81a273a924b3585eedc0a0a3ea24b
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08969570B2

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