Ammonium Chloride → HCID 17917865、化合物

HRID 1920193ノート

反応式

HRID 1920193 の反応式
[CH:1]12[O:7][CH:6]1[CH2:5][CH2:4][N:3]([C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])[CH2:2]2.[N-:18]=[N+:19]=[N-:20].[Na+].[Cl-].[NH4+]>CO.O>[N:18]([CH:1]1[CH:6]([OH:7])[CH2:5][CH2:4][N:3]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:2]1)=[N+:19]=[N-:20].[N:18]([CH:6]1[CH2:5][CH2:4][N:3]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:2][CH:1]1[OH:7])=[N+:19]=[N-:20]

参加物

7

反応物 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 13186888Benzyl 7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate

生成物 2

HCID 17917865HCID 17917865、化合物HCID 59455704HCID 59455704、化合物

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

反応条件

温度
65 °C

実験手順

To a solution of benzyl 7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate (1.0 equiv.) in MeOH and water (0.17M) was added sodium azide (2.0 equiv.) and ammonium chloride (1.0 equiv.). The reaction was stirred at 65° C. in an oil bath for 7 h, then concentrated to remove the methanol. Ethyl acetate was added, the organic phase was separated, dried with Na2SO4, and concentrated under vacuo to give benzyl 3-azido-4-hydroxypiperidine-1-carboxylate and benzyl 4-azido-3-hydroxypiperidine-1-carboxylate as a clear oil in >95% yield. LCMS (m/z): 276.9 (MH+), Rt=2.98 min.

後処理

  1. concentrationconcentrated
  2. customto remove the methanol
  3. additionEthyl acetate was added
  4. customthe organic phase was separated
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated under vacuo

出典と根拠

ORDレコード
ord-3fb5c2fbc08d4e079f0c57c230dde1bd
出典データセット
uspto-grants-2012_05
特許番号
US08168794B2

反応ノート

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