Oxalic Acid → (2R)-N-(piperidin-4-yl)oxolane-2-carboxamide

HRID 2079368노트

반응식

HRID 2079368 반응식
C([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]([C@H:17]2[CH2:21][CH2:20][CH2:19][O:18]2)=[O:16])[CH2:10][CH2:9]1)C1C=CC=CC=1.[H][H].C(O)(=O)C(O)=O>C(O)C.C(O)(=O)C.[Pd].CC(O)C>[NH:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]([C@H:17]2[CH2:21][CH2:20][CH2:19][O:18]2)=[O:16])[CH2:10][CH2:9]1

참가 물질

8

반응물 3

HCID 971Oxalic AcidHCID 1246648(R)-tetrahydrofuran-2-carboxylic acid (1-benzyl-piperidin-4-yl)-amideHCID 178418361HCID 178418361, 화합물2회

생성물 1

HCID 28810902(2R)-N-(piperidin-4-yl)oxolane-2-carboxamide

시약·촉매·용매 4

HCID 23938Palladium촉매HCID 176Acetic Acid용매HCID 702Ethanol용매HCID 3776Isopropanol용매

실험 절차

(R)-Tetrahydro-furan-2-carboxylic acid (1-benzyl-piperidin-4-yl)-amide (128 g, 444 mmol) was dissolved in 300 mL ethanol and 50 mL acetic acid. Palladium on activated carbon (5 g) was added. A hydrogen pressure of 5 bars was applied, and hydrogenation was continued until no more hydrogen was consumed (about 5 days). The suspension was filtered through Celite, and the filtrate was evaporated to dryness under reduced pressure. The residue and oxalic acid (50 g, 555 mmol) were suspended in 500 mL 2-propanol and heated to dissolve the solids. Upon cooling, the oxalate salt of R-tetrahydro-furan-2-carboxylic acid piperidin-4-ylamide crystallized and was collected by filtration to yield (R)-Tetrahydro-furan-2-carboxylic acid piperidin-4-ylamide as an oxalate salt (99.0 g, 77%) as an off-white solid. 1H-NMR (300 MHz, DMSO-d6): δ 7.84 (d, J=7.8 Hz, 1H), 5.90 (bs, 2H), 4.18-4.14 (m, 1H), 3.89-3.67 (m, 3H), 3.25-3.20 (m, 2H), 2.94-2.71 (m, 2H), 2.13-2.00 (m, 1H), 1.56-1.58 (m, 6H) ppm.

후처리

  1. customwas consumed (about 5 days)
  2. filtrationThe suspension was filtered through Celite
  3. customthe filtrate was evaporated to dryness under reduced pressure
  4. temperatureheated
  5. dissolutionto dissolve the solids
  6. temperatureUpon cooling
  7. customthe oxalate salt of R-tetrahydro-furan-2-carboxylic acid piperidin-4-ylamide crystallized
  8. filtrationwas collected by filtration

출처 및 근거

ORD 기록
ord-0271cc4d19f4432b927f11a8134a68dc
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07928107B2

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