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

HRID 1398023노트

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HRID 1398023 반응식
[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]

참가 물질

7

반응물 2

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

생성물 1

HCID 19691305Phenylmethyl 3-azido-4-hydroxy-1-pyrrolidinecarboxylate수율 65.9%

시약·촉매·용매 4

HCID 180Acetone용매HCID 962Water용매2회HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-a3e5487e861d4499b52363294d44328a
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901307B2

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