Sodium borohydride → tert-Butyl 4-hydroxy-3-(hydroxymethyl)piperidine-1-carboxylate

HRID 402059

반응식

HRID 402059 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+]>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

4

반응물 2

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

생성물 1

HCID 66717856tert-Butyl 4-hydroxy-3-(hydroxymethyl)piperidine-1-carboxylate

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 (51.59 mmol, 14 g) in methanol (300 mL) was added sodium borohydride (12 g) in 12 portions over 30 min. The reaction mixture was stirred for additional 30 min, and the volatiles were removed under reduced pressure. To the residue was added saturated ammonium chloride (300 mL). The mixture was extracted with ethyl acetate (300 mL), and the organic layer was dried and concentrated under reduced pressure. The residue was purified on a flash silica gel column eluting with ethyl acetate to provide 4-hydroxy-3-hydroxymethyl-piperidine-1-carboxylic acid tert-butyl ester.

후처리

  1. customthe volatiles were removed under reduced pressure
  2. additionTo the residue was added saturated ammonium chloride (300 mL)
  3. extractionThe mixture was extracted with ethyl acetate (300 mL)
  4. customthe organic layer was dried
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified on a flash silica gel column
  7. washeluting with ethyl acetate

출처 및 근거

ORD 기록
ord-f3c4b0b8e57247ada3a7d2c81bc38f3f
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08741900B2

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