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

HRID 412658ノート

反応式

HRID 412658 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-bd888f360c7347f2a214c17af0425286
出典データセット
uspto-grants-2003_05
特許番号
US06562964B1

反応ノート

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