Sodium Hydroxide → (S)-(1-Benzyl-3-methylpiperidin-3-yl)methanol

HRID 2407313노트

반응식

HRID 2407313 반응식
C([O:3][C:4]([C@@:6]1([CH3:19])[CH2:11][CH2:10][CH2:9][N:8]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:7]1)=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>C1COCC1>[CH2:12]([N:8]1[CH2:9][CH2:10][CH2:11][C@@:6]([CH2:4][OH:3])([CH3:19])[CH2:7]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 66727374(S)-1-Benzyl-3-methylpiperidine-3-carboxylic acid ethyl ester

생성물 1

HCID 66727443(S)-(1-Benzyl-3-methylpiperidin-3-yl)methanol수율 93.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

(S)-1-Benzyl-3-methylpiperidine-3-carboxylic acid ethyl ester (1.64 g, 6.3 mmol) in dry THF (20 ml) was slowly added to a stirred suspension of LiAlH4 (0.71 g, 18.8 mmol) in dry THF (20 ml) under nitrogen atmosphere. After the addition the mixture was refluxed for 1.5 h. The solution was cooled with an ice bath, stirred vigorously and 2.5 M NaOH was added carefully drop by drop until no reaction occurred and a white precipitate was formed. The solvent was decanted and the solid washed with EtOAc (2×20 ml). The combined organic phases were dried, filtered and evaporated to dryness to give 1.29 g of the alcohol product as a white powder.

후처리

  1. additionAfter the addition the mixture
  2. temperaturewas refluxed for 1.5 h
  3. temperatureThe solution was cooled with an ice bath
  4. customa white precipitate was formed
  5. customThe solvent was decanted
  6. washthe solid washed with EtOAc (2×20 ml)
  7. customThe combined organic phases were dried
  8. filtrationfiltered
  9. customevaporated to dryness

출처 및 근거

ORD 기록
ord-8d1c5d008ef140c480740d56ddc5a997
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08809536B2

반응 노트

불러오는 중…