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Sodium borohydride → Tert-butyl 4-hydroxy-2-methylpiperidine-1-carboxylate

HRID 386534
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HRID 386534 반응식
[CH3:1][CH:2]1[CH2:7][C:6](=[O:8])[CH2:5][CH2:4][N:3]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].[BH4-].[Na+]>CO>[OH:8][CH:6]1[CH2:5][CH2:4][N:3]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH:2]([CH3:1])[CH2:7]1
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참가 물질

4

반응물 2

HCID 4311764Sodium borohydrideHCID 12992764tert-Butyl 2-methyl-4-oxopiperidine-1-carboxylate

생성물 1

HCID 22181172Tert-butyl 4-hydroxy-2-methylpiperidine-1-carboxylate수율 101.5%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
0 °C

실험 절차

To a solution of tert-butyl 2-methyl-4-oxopiperidine-1-carboxylate (727 mg, 3.41 mmol, Small Molecules Inc.) in MeOH (6.0 mL) at 0° C. was added sodium borohydride (193 mg, 5.11 mmol, Aldrich) in several portions. The reaction mixture was stirred at 0° C. for 1 hr and warmed up to room temperature and continuously stirred for another 2.5 hrs. The resulting mixture was then quenched with saturated NH4Cl aqueous solution and evaporated under reduced pressure to remove MeOH followed by extraction with CH2Cl2 (3×). The combined extracts were dried (Na2SO4) and concentrated in vacuo to give the title compound (745 mg) as a colorless sticky oil which was used without further purification.

후처리

  1. temperaturewarmed up to room temperature
  2. stirringcontinuously stirred for another 2.5 hrs
  3. customThe resulting mixture was then quenched with saturated NH4Cl aqueous solution
  4. customevaporated under reduced pressure
  5. customto remove MeOH
  6. extractionfollowed by extraction with CH2Cl2 (3×)
  7. dry with materialThe combined extracts were dried (Na2SO4)
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-1b1d7a841b854dd2856015d2459a8921
출처 데이터셋
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08372837B2

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