4-(7-fluoro-3-methoxycarbonylmethyl-naphthalen-1-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester → 4-(7-Fluoro-3-methoxycarbonylmethyl-naphthalen-1-yl)-piperidine-1-carboxylic acid tert-butyl ester

HRID 2363813ノート

反応式

HRID 2363813 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([F:24])[CH:22]=3)[CH:17]=[C:16]([CH2:25][C:26]([O:28][CH3:29])=[O:27])[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>[Pd].C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([F:24])[CH:22]=3)[CH:17]=[C:16]([CH2:25][C:26]([O:28][CH3:29])=[O:27])[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

4

反応物 1

HCID 866868854-(7-fluoro-3-methoxycarbonylmethyl-naphthalen-1-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 866868864-(7-Fluoro-3-methoxycarbonylmethyl-naphthalen-1-yl)-piperidine-1-carboxylic acid tert-butyl ester収率 62.3%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

10% Palladium on carbon (0.09 g) was added to a deoxygenated solution of 4-(7-fluoro-3-methoxycarbonylmethyl-naphthalen-1-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (which may be prepared as described above; 0.64 g, 1.6 mmol) in ethanol (30 mL) in a Parr shaker vessel. The mixture was hydrogenated at 60 psi for 16 h and then filtered through a pad of celite. The celite was washed with ethanol (2×5 mL) and the combined filtrates were concentrated under reduced pressure. The residue was purified by silica gel column chromatography (100-200 mesh), using 20% ethyl acetate/hexanes as eluent, to give 4-(7-fluoro-3-methoxycarbonylmethyl-naphthalen-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (0.40 g, 62%) as a sticky colorless solid. MS cald. for C23H29FNO4 [(M+H)+] 402, obsd. 402.4.

後処理

  1. filtrationfiltered through a pad of celite
  2. washThe celite was washed with ethanol (2×5 mL)
  3. concentrationthe combined filtrates were concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (100-200 mesh)

出典と根拠

ORDレコード
ord-7e7138ce7e31482580b94871cc909802
出典データセット
uspto-grants-2014_04
特許番号
US08691993B2

反応ノート

読み込み中…