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

HRID 1011885ノート

反応式

HRID 1011885 の反応式
[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

参加物

5

反応物 2

HCID 2723923Ammonium formateHCID 235336103-Methoxyoxan-4-one

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 22242641Methanol--water (1/1)溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-2eb6a603fa684f3499509ee92512c2cb
出典データセット
uspto-grants-2011_07
特許番号
US07977358B2

反応ノート

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