Ammonium Chloride → tert-Butyl 4-hydroxy-3-(hydroxymethyl)piperidine-1-carboxylate

HRID 2168660노트

반응식

HRID 2168660 반응식
C([O:3][C:4]([CH:6]1[C:11](=[O:12])[CH2:10][CH2:9][N:8]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:7]1)=O)C.[BH4-].[Na+].[NH4+].[Cl-]>CO>[C:16]([O:15][C:13]([N:8]1[CH2:9][CH2:10][CH:11]([OH:12])[CH:6]([CH2:4][OH:3])[CH2:7]1)=[O:14])([CH3:19])([CH3:18])[CH3:17]

참가 물질

5

반응물 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 64208761-(1,1-Dimethylethyl) 3-ethyl 4-oxo-1,3-piperidinedicarboxylate

생성물 1

HCID 66717856tert-Butyl 4-hydroxy-3-(hydroxymethyl)piperidine-1-carboxylate수율 84.6%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a stirred solution of 4-oxo-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester (14 g) in MeOH (300 mL) was added NaBH4 (12 g) in 12 lots over 1 h period. After completion of addition, the reaction mixture was stirred for 30 min. Removed solvent under reduced pressure, to the residue was added saturated NH4Cl solution (300 mL) and was extracted with EtOAc (300 mL). The organic layer was dried, filtered and concentrated under reduced pressure. The residue was purified by flash silica gel column chromatography by eluting with ethyl acetate to give 4-hydroxy-3-hydroxymethyl-piperidine-1-carboxylic acid tert-butyl ester (10.1 g, cis/trans mixture).

후처리

  1. additionAfter completion of addition
  2. extractionwas extracted with EtOAc (300 mL)
  3. customThe organic layer was dried
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash silica gel column chromatography
  7. washby eluting with ethyl acetate

출처 및 근거

ORD 기록
ord-601b0b9f551647ccbbf67337d1eab512
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09045461B2

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