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Ammonium formate → (S)-3-Methyl-3-[2-(tetrahydropyran-2-yloxy)ethoxymethyl]piperidine

HRID 453820
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HRID 453820 반응식
C([N:8]1[CH2:13][CH2:12][CH2:11][C@:10]([CH3:25])([CH2:14][O:15][CH2:16][CH2:17][O:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][O:20]2)[CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[Pd]>[CH3:25][C@:10]1([CH2:14][O:15][CH2:16][CH2:17][O:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][O:20]2)[CH2:11][CH2:12][CH2:13][NH:8][CH2:9]1
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참가 물질

5

반응물 2

HCID 2723923Ammonium formateHCID 66727401(S)-1-Benzyl-3-methyl-3-[2-(tetrahydropyran-2-yloxy)ethoxymethyl]piperidine

생성물 1

HCID 66727215(S)-3-Methyl-3-[2-(tetrahydropyran-2-yloxy)ethoxymethyl]piperidine수율 83.6%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매2회

실험 절차

(S)-1-Benzyl-3-methyl-3-[2-(tetrahydropyran-2-yloxy)ethoxymethyl]piperidine (1.14 g, 3.3 mmol) in MeOH (11 ml) was added to a suspension of Pd/C (0.23 g) in MeOH (11 ml), followed by ammonium formate (1.03 g, 16.4 mmol). The mixture was refluxed for 2 h, after which it was cooled and filtered through Celite. The catalyst was washed with DCM and the combined organic phases were evaporated to dryness. To the residue was added brine (15 ml) and the solution was extracted with EtOAc (3×30 ml). The extracts were combined, dried, filtered and evaporated to yield 0.71 g of the debenzylated product.

후처리

  1. temperatureThe mixture was refluxed for 2 h
  2. temperatureafter which it was cooled
  3. filtrationfiltered through Celite
  4. washThe catalyst was washed with DCM
  5. customthe combined organic phases were evaporated to dryness
  6. additionTo the residue was added brine (15 ml)
  7. extractionthe solution was extracted with EtOAc (3×30 ml)
  8. customdried
  9. filtrationfiltered
  10. customevaporated

출처 및 근거

ORD 기록
ord-1a2fdf57a64b4c0497f82f91a11bc1c1
출처 데이터셋
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08492549B2

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