Ammonium formate → cis-(3-Methoxy-tetrahydro-pyran-4-yl)-methyl-amine

HRID 1011885노트

반응식

HRID 1011885 반응식
[CH3:1][O:2][CH:3]1[C:8](=O)[CH2:7][CH2:6][O:5][CH2:4]1.[CH:10]([O-])=O.[NH4+:13]>[Pd].O.CO>[CH3:1][O:2][C@H:3]1[C@@H:8]([NH:13][CH3:10])[CH2:7][CH2:6][O:5][CH2:4]1

참가 물질

5

반응물 2

HCID 2723923Ammonium formateHCID 235336103-Methoxyoxan-4-one

생성물 1

HCID 67314240cis-(3-Methoxy-tetrahydro-pyran-4-yl)-methyl-amine수율 49%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 22242641Methanol--water (1/1)용매

실험 절차

A slurry of 3-methoxy-tetrahydro-pyran-4-one (0.4 g, 3 mmol-described in WO03/093266(A1)), ammonium formate (1.9 g, 30 mmol), 10% palladium on charcoal (1 g) in water:MeOH (1:5, 6 ml) was stirred overnight after which time it was filtered through Hyflo, the mixture concentrated to remove the MeOH, the residue taken up in Et2O, dried (Na2SO4) and concentrated to afford the title product (0.2 g, 49%) as a yellow oil (contaminated by 10-20% of the trans isomer). 1H NMR (300 MHz, CDCl3) (cis isomer) δ 1.60-1.80 (2H, m), 2.95-3.00 (1H, m), 3.22-3.43 (5H, m). 3.82-3.95 (1H, m), 4.01-4.13 (1H, m).

후처리

  1. filtrationwas filtered through Hyflo
  2. concentrationthe mixture concentrated
  3. customto remove the MeOH
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-2eb6a603fa684f3499509ee92512c2cb
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07977358B2

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