Nitrogen → (S)-Tetrahydrofuran-3-yl (3-aminobenzyl)carbamate

HRID 503967ノート

反応式

HRID 503967 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]([CH:17]=[CH:18][CH:19]=1)[CH2:7][NH:8][C:9](=[O:16])[O:10][C@H:11]1[CH2:15][CH2:14][O:13][CH2:12]1)([O-])=O.N#N>CCOC(C)=O.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([CH:17]=[CH:18][CH:19]=1)[CH2:7][NH:8][C:9](=[O:16])[O:10][C@H:11]1[CH2:15][CH2:14][O:13][CH2:12]1

参加物

5

反応物 2

HCID 947Nitrogen4 回HCID 57718888(S)-Tetrahydrofuran-3-yl (3-nitrobenzyl)carbamate

生成物 1

HCID 59901461(S)-Tetrahydrofuran-3-yl (3-aminobenzyl)carbamate

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 8857Ethyl Acetate溶媒

実験手順

Charged 15 g of (S)-tetrahydrofuran-3-yl 3-nitrobenzylcarbamate 2c in 120 ml EtOAc to a 1L Parr bomb at room temperature under a blanket of N2. The agitator was started and the vessel pressurized with N2 to 0.75 bar, then the pressure was released. This procedure was repeated 3 times, then the agitator was stopped before adding 0.225 g of 5% Pd/C. The agitator was started, the vessel pressurized with N2 to 0.75 bar, then the pressure was released. This procedure was repeated 3 times, then the agitator was stopped. The vessel was pressurized with H2 to 2 bar, then the pressure was released. This procedure was repeated 3 times, then the vessel was pressurized with H2 to 6.75 bar. The agitator was started and the suspension stirred until complete conversion was evident by HPLC. The H2 pressure was released, the vessel re-pressurized with N2 to 0.75 bar, then the pressure was released. This procedure was repeated 3 times then the agitator was stopped, the reaction mixture filtered through celite and the filter cake rinsed with 30 ml EtOAc to give crude (S)-tetrahydrofuran-3-yl 3-aminobenzylcarbamate 2d as a solution in EtOAc that was used as is immediately in the next step.

後処理

  1. filtrationthe reaction mixture filtered through celite
  2. washthe filter cake rinsed with 30 ml EtOAc

出典と根拠

ORDレコード
ord-9b64884eb66e4127adbe40b8045d357a
出典データセット
uspto-grants-2010_08
特許番号
US07777048B2

反応ノート

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