Sodium Azide → tert-butyl (2S,4R)-4-azido-2-[(benzyloxy)methyl]pyrrolidine-1-carboxylate

HRID 412658노트

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HRID 412658 반응식
[N-:1]=[N+:2]=[N-:3].[Na+].[CH2:5]([O:12][CH2:13][C@@H:14]1[CH2:18][C@H:17](OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:16][N:15]1[C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C(O)C.CN(C)C=O>[N:1]([C@H:17]1[CH2:16][N:15]([C:30]([O:32][C:33]([CH3:35])([CH3:34])[CH3:36])=[O:31])[C@H:14]([CH2:13][O:12][CH2:5][C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:18]1)=[N+:2]=[N-:3]

참가 물질

5

반응물 2

HCID 33557Sodium AzideHCID 57077697tert-Butyl (2S,4S)-2-[(benzyloxy)methyl]-4-[(4-methylphenyl)sulfonyl]oxypyrrolidine-1-carboxylate

생성물 1

HCID 57019743tert-butyl (2S,4R)-4-azido-2-[(benzyloxy)methyl]pyrrolidine-1-carboxylate수율 99%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

Sodium azide (0.32 g) was added to a solution of tert-Butyl (2S,4S)-2-[(benzyloxy)methyl]-4-[(4-methylphenyl)sulfonyl]oxypyrrolidine-1-carboxylate (1.15 g) [see Preparation 32] in ethanol (20 ml) and dimethylformamide (5 ml). The reaction mixture was heated to 80° C. for 4 hours, after which time the cooled mixture was partitioned between diethyl ether and water. The organic layer was separated and the aqueous extracted twice with diethyl ether, the combined organic layers were dried over magnesium sulphate and the solvent removed under reduced pressure. The residue was azeotroped with dichloromethane to afford tert-butyl (2S,4R)-4-azido-2-[(benzyloxy)methyl]pyrrolidine-1-carboxylate (820 mg) as an oil.

후처리

  1. customafter which time the cooled mixture was partitioned between diethyl ether and water
  2. customThe organic layer was separated
  3. extractionthe aqueous extracted twice with diethyl ether
  4. dry with materialthe combined organic layers were dried over magnesium sulphate
  5. customthe solvent removed under reduced pressure
  6. customThe residue was azeotroped with dichloromethane

출처 및 근거

ORD 기록
ord-bd888f360c7347f2a214c17af0425286
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06562964B1

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