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

HRID 1406845노트

반응식

HRID 1406845 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

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 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.

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-e343bdaf23d742e3afede27aeed9955f
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08916709B2

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