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

HRID 503967노트

반응식

HRID 503967 반응식
[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

참가 물질

5

반응물 2

HCID 947Nitrogen4회HCID 57718888(S)-Tetrahydrofuran-3-yl (3-nitrobenzyl)carbamate

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-9b64884eb66e4127adbe40b8045d357a
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07777048B2

반응 노트

불러오는 중…