Ethyl Acetate → [2S,3S]-1-(4-azidobut-2-yn-1-yl)-2-phenyl-3-[3-(1-methyl-1H-[1,2,3]triazol5-yl)-5-(trifluoromethyl)phenylmethoxy]piperidine

HRID 355378ノート

反応式

HRID 355378 の反応式
Cl[CH2:2][C:3]#[C:4][CH2:5][N:6]1[CH2:11][CH2:10][CH2:9][C@H:8]([O:12][CH2:13][C:14]2[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[C:16]([C:24]3[N:28]([CH3:29])[N:27]=[N:26][CH:25]=3)[CH:15]=2)[C@@H:7]1[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.[N-:36]=[N+:37]=[N-:38].[Na+].[Cl-].[NH4+].C(OCC)(=O)C>CS(C)=O>[N:36]([CH2:2][C:3]#[C:4][CH2:5][N:6]1[CH2:11][CH2:10][CH2:9][C@H:8]([O:12][CH2:13][C:14]2[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[C:16]([C:24]3[N:28]([CH3:29])[N:27]=[N:26][CH:25]=3)[CH:15]=2)[C@@H:7]1[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[N+:37]=[N-:38]

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 18666489[2S,3S]-1-(4-chlorobut-2-yn-1-yl)-2-phenyl-3-[3-(1-methyl-1H-[1,2,3]triazol-5-yl)-5-(trifluoromethyl)phenylmethoxy]piperidine

生成物 1

HCID 18666488[2S,3S]-1-(4-azidobut-2-yn-1-yl)-2-phenyl-3-[3-(1-methyl-1H-[1,2,3]triazol5-yl)-5-(trifluoromethyl)phenylmethoxy]piperidine収率 83.4%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

To a solution of [2S,3S]-1-(4-chlorobut-2-yn-1-yl)-2-phenyl-3-[3-(1-methyl-1H-[1,2,3]triazol-5-yl)-5-(trifluoromethyl)phenylmethoxy]piperidine (142 mg) in dimethyl sulphoxide (3.0 ml) was added sodium azide (20.1 mg). The solution was stirred for 3 hours at room temperature at which time aqueous ammonium chloride and ethyl acetate were added. The organic phase was separated, washed with water (20 ml), saturated brine (20 ml) dried over MgSO4, filtered and the solvent removed under reduced pressure. Purification by MPLC (20% ethyl acetate/hexane) gave [2S,3S]-1-(4-azidobut-2-yn-1-yl)-2-phenyl-3-[3-(1-methyl-1H-[1,2,3]triazol5-yl)-5-(trifluoromethyl)phenylmethoxy]piperidine as a white solid (120 mg). 1H NMR (360 MHz,CDCl3) δ 1.20-1.60 (2H, m), 2.22 (2H, m), 2.67 (1H, m), 2.98 (1H, m), 3.27 (2H, m), 3.47 (1H, br s), 3.62 (1H, br s), 3.92 (2H, s), 3.98 (3H, s), 4.47 (1H, d, J=11.0 Hz), 4.81 (1H, d, J=11.0 Hz), 7.26-7.35 (4H, m), 7.44-7.47 (4H, m), 7.69 (1H, s).

後処理

  1. additionwere added
  2. customThe organic phase was separated
  3. washwashed with water (20 ml), saturated brine (20 ml)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent removed under reduced pressure
  7. customPurification by MPLC (20% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-a751e53a382344668baaa638e9c662dd
出典データセット
uspto-grants-1998_11
特許番号
US05830892

反応ノート

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