Hydrochloric Acid → tert-butyl (3RS,4RS)-3-(1,4-dimethoxy-naphthalen-2-ylmethoxy)-4-(4-hydroxy-phenyl)-piperidine-1-carboxylate

HRID 1005248ノート

反応式

HRID 1005248 の反応式
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH:12]2[O:24][CH2:25][C:26]2[CH:35]=[C:34]([O:36][CH3:37])[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:27]=2[O:38][CH3:39])=[CH:7][CH:6]=1)C=C.N12CCN(CC1)CC2.Cl>C(O)C.CC(O)=O.CC(O)=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[CH3:39][O:38][C:27]1[C:28]2[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:34]([O:36][CH3:37])=[CH:35][C:26]=1[CH2:25][O:24][CH:12]1[CH:11]([C:8]2[CH:7]=[CH:6][C:5]([OH:4])=[CH:10][CH:9]=2)[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13]1

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 9237DabcoHCID 53648544tert-butyl (3RS,4RS)-4-(4-allyloxy-phenyl)-3-(1,4-dimethoxy-naphthalen-2-ylmethoxy)-piperidine-1-carboxylate

生成物 1

HCID 54373685tert-butyl (3RS,4RS)-3-(1,4-dimethoxy-naphthalen-2-ylmethoxy)-4-(4-hydroxy-phenyl)-piperidine-1-carboxylate収率 91%

試薬・触媒・溶媒 2

HCID 10865532Bis(triphenylphosphine)palladium(II) diacetate触媒HCID 702Ethanol溶媒

反応条件

温度
2.5 °C

実験手順

A solution of 315 mg (0.59 mmol) of tert-butyl (3RS,4RS)-4-(4-allyloxy-phenyl)-3-(1,4-dimethoxy-naphthalen-2-ylmethoxy)-piperidine-1-carboxylate, 44 mg (0.059 mmol) of bis-(triphenylphosphine)-palladium(II) diacetate and 132 mg (1.18 mmol) of 1,4-diazabicyclo [2.2.2]octane in 10 ml of 95% ethanol was heated to reflux under argon for 2 hours. Subsequently, the reaction mixture was cooled to 0-5° C. and treated with 0.6 ml of 1N hydrochloric acid. Thereafter, the solvent was distilled off under reduced pressure and the residue was partitioned between ethyl acetate and water. After extraction and drying of the organic phase over sodium sulphate it was evaporated under reduced pressure. The residue was purified on silica gel using a 9:1 mixture of methylene chloride and ether as the eluent. There were obtained 265 mg (91% of theory) of tert-butyl (3RS,4RS)-3-(1,4-dimethoxy-naphthalen-2-ylmethoxy)-4-(4-hydroxy-phenyl)-piperidine-1-carboxylate as a yellowish foam; MS: 494 (M+H)+.

後処理

  1. temperatureto reflux under argon for 2 hours
  2. distillationThereafter, the solvent was distilled off under reduced pressure
  3. customthe residue was partitioned between ethyl acetate and water
  4. extractionAfter extraction
  5. dry with materialdrying of the organic phase over sodium sulphate it
  6. customwas evaporated under reduced pressure
  7. customThe residue was purified on silica gel using
  8. additiona 9:1 mixture of methylene chloride and ether as the eluent

出典と根拠

ORDレコード
ord-2149c1d500ed40cf9a2695ccd96043d8
出典データセット
uspto-grants-2000_04
特許番号
US06051712

反応ノート

読み込み中…