Methanol → Benzyl 5-hydroxy-2-methylpiperidine-1-carboxylate

HRID 1749369노트

반응식

HRID 1749369 반응식
C1COCC1.CO.[Li+].[BH4-].[CH3:10][CH:11]1[CH2:16][CH2:15][C:14](=[O:17])[CH2:13][N:12]1[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19]>CC(C)=O>[CH2:21]([O:20][C:18]([N:12]1[CH2:13][CH:14]([OH:17])[CH2:15][CH2:16][CH:11]1[CH3:10])=[O:19])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

참가 물질

6

반응물 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 4148881Lithium borohydrideHCID 71305938Benzyl 2-methyl-5-oxopiperidine-1-carboxylate

생성물 1

HCID 71305932Benzyl 5-hydroxy-2-methylpiperidine-1-carboxylate

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

To a solution of THF (200 mL) and MeOH (11 mL) was added LiBH4 (2 M, 89 mL, 0.18 mol). Some gas evolution and small exotherm were observed. The reaction was aged at room temperature for 30 min before being cooled to −10° C. with an acetone:ice bath. ±benzyl 2-methyl-5-oxopiperidine-1-carboxylate (22.0 g, 0.089 mol) was then added dropwise, keeping the temperature below −5° C. The reaction was then aged at −10° C. for 30 min. The reaction was quenched by adding half-saturated, aqueous NaHCO3, then extracted with EtOAc. The layers were separated and the organics dried with MgSO4. The organics were concentrated to give the titled compound as a crude, colorless oil.

후처리

  1. customthe temperature below −5° C
  2. waitThe reaction was then aged at −10° C. for 30 min
  3. customThe reaction was quenched
  4. additionby adding half-saturated
  5. extractionaqueous NaHCO3, then extracted with EtOAc
  6. customThe layers were separated
  7. dry with materialthe organics dried with MgSO4
  8. concentrationThe organics were concentrated

출처 및 근거

ORD 기록
ord-522d2eeaab7c42bca6839abc49fd9316
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09156819B2

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