Triphenylphosphine → N-carbobenzyloxy-4-(cis)-(4-cyanophenoxy)-L-proline methyl ester

HRID 1769277

反応式

HRID 1769277 の反応式
[CH3:1][O:2][C:3](=[O:20])[C@@H:4]1[CH2:8][C@@H:7]([OH:9])[CH2:6][N:5]1[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:40]([C:42]1[CH:47]=[CH:46][C:45](O)=[CH:44][CH:43]=1)#[N:41].CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH3:1][O:2][C:3](=[O:20])[C@@H:4]1[CH2:8][C@H:7]([O:9][C:45]2[CH:46]=[CH:47][C:42]([C:40]#[N:41])=[CH:43][CH:44]=2)[CH2:6][N:5]1[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11]

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 130194-CyanophenolHCID 6884112-Methyl 1-(phenylmethyl) (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylateHCID 5462977Diethyl azodicarboxylate

生成物 1

HCID 18654599N-carbobenzyloxy-4-(cis)-(4-cyanophenoxy)-L-proline methyl ester収率 89%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a solution of N-carbobenzyloxy-trans-4-hydroxy-L-proline methyl ester (10.0 g, 35.8 mmol) in 200 mL of anhydrous THF under N2 was added triphenylphosphine (10.6 g, 39.4 mmol) and 4-cyanophenol (4.7 g, 39.4 mmol). This solution was cooled to 0° C. and then treated with diethylazodicarboxylate (6.3 mL, 39.4 mmol), added dropwise over 30 minutes. The reaction was warmed to room temperature and stirred for 2 days. The solvent was removed in vacuo, and the residue chromatographed (SiO2, 30% ethyl acetate/hexanes) to provide 12.1 g (89%) of N-carbobenzyloxy-4-(cis)-(4-cyanophenoxy)-L-proline methyl ester as a colorless oil. (MS).

後処理

  1. additionadded dropwise over 30 minutes
  2. temperatureThe reaction was warmed to room temperature
  3. customThe solvent was removed in vacuo
  4. customthe residue chromatographed (SiO2, 30% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-ac690719893f46f19430c33aa10f4bd1
出典データセット
uspto-grants-1995_01
特許番号
US05380866

関連ノート

読み込み中…