Sodium Azide → Phenylmethyl 3-azido-4-hydroxy-1-pyrrolidinecarboxylate

HRID 1398023ノート

反応式

HRID 1398023 の反応式
[CH:1]12[O:6][CH:5]1[CH2:4][N:3]([C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])[CH2:2]2.[N-:17]=[N+:18]=[N-:19].[Na+]>CN(C=O)C.CC(C)=O.O.CCOCC>[N:17]([CH:1]1[CH:5]([OH:6])[CH2:4][N:3]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:2]1)=[N+:18]=[N-:19]

参加物

7

反応物 2

HCID 33557Sodium AzideHCID 22147363Benzyl 6-oxa-3-azabicyclo(3.1.0)hexane-3-carboxylate

生成物 1

HCID 19691305Phenylmethyl 3-azido-4-hydroxy-1-pyrrolidinecarboxylate収率 65.9%

試薬・触媒・溶媒 4

HCID 180Acetone溶媒HCID 962Water溶媒2 回HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

To a stirred mixture of benzyl 6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate (5.2 g, 23.72 mmol) (Method 197) in DMF (30 mL) was added sodium azide (2.313 g, 35.58 mmol) in a mixture of acetone (20.00 mL) and water (10.00 mL). The resulting mixture was stirred at 80° C. for 24 h. The mixture was then diluted with water and ether, separated, and the organic layer was washed with brine, dried and conc. in vacuo. The resulting material was purified via silica gel chromatography (eluted with 15% to 35% ethyl acetate/hexane), yielding the title compound as a yellow solid (4.10 g, 65.9%). 1H NMR (400 MHz, dichloromethane-d2) δ ppm 7.50-7.25 (m, 5 H), 5.43-5.25 (m, 2 H), 4.31 (brs, 1 H), 4.00 (brs, 1 H), 3.77 (dd, 1 H), 3.69 (dd, 1 H), 3.53 (d, 1 H), 3.44 (dd, 1 H), 2.17 (brs, 1 H); m/z 263.

後処理

  1. customseparated
  2. washthe organic layer was washed with brine
  3. customdried and conc. in vacuo
  4. customThe resulting material was purified via silica gel chromatography (eluted with 15% to 35% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-a3e5487e861d4499b52363294d44328a
出典データセット
uspto-grants-2014_12
特許番号
US08901307B2

反応ノート

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