Tert-butyl 4-(2-methoxy-2-oxoethylidene)piperidine-1-carboxylate → tert-Butyl 4-(2-methoxy-2-oxoethyl)piperidine-1-carboxylate

HRID 132200

반응식

HRID 132200 반응식
[CH3:1][O:2][C:3](=[O:18])[CH:4]=[C:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1.[H][H]>C(OCC)(=O)C.CO.[Pd]>[CH3:1][O:2][C:3](=[O:18])[CH2:4][CH:5]1[CH2:6][CH2:7][N:8]([C:11]([O:13][C:14]([CH3:16])([CH3:15])[CH3:17])=[O:12])[CH2:9][CH2:10]1

참가 물질

6

반응물 2

HCID 10377658Tert-butyl 4-(2-methoxy-2-oxoethylidene)piperidine-1-carboxylateHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 1514280tert-Butyl 4-(2-methoxy-2-oxoethyl)piperidine-1-carboxylate수율 97%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 887Methanol용매HCID 8857Ethyl Acetate용매

실험 절차

tert-Butyl 4-(2-methoxy-2-oxoethylidene)piperidine-1-carboxylate (35.71 g, 140 mmol) was dissolved in a mixture of ethyl acetate (110 mL) and methanol (110 mL). 50% wet 10% palladium on carbon (3.3 g) was added to the mixture. Reaction vessel was charged with 55 psi of hydrogen gas. Reaction shook on a Parr apparatus at room temperature for 16 hours. Reaction mixture was filtered to remove the catalyst. Filtrate was concentrated in vacuo. Title compound was obtained as clear colorless oil in 97% yield. 1H NMR (300 MHz, CDCl3): δ=4.04 (d, J=10.25, 2H), 3.64 (s, 3H), 2.68 (t, J=12.44, 2H), 2.21 (d, J=6.95, 2H), 1.98-1.77 (m, 1H), 1.64 (d, J=13.54, 2H), 1.41 (s, 9H), 1.25-0.99 (m, 2H).

후처리

  1. customReaction vessel
  2. customReaction
  3. customReaction mixture
  4. filtrationwas filtered
  5. customto remove the catalyst
  6. concentrationFiltrate was concentrated in vacuo

출처 및 근거

ORD 기록
ord-147cf76ce6814cbcbb42449da14866f2
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07384930B2

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