Benzylamine → 3-Amino-1-benzylpyrrolidine-3-carbonitrile

HRID 1609826ノート

反応式

HRID 1609826 の反応式
[CH2:1]([N:8]1[CH2:12][CH2:11][C:10]([NH:15]C(=O)C(O)CC(C)C)([C:13]#[N:14])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC(OC1C=CC([N+]([O-])=O)=CC=1)=O.CN1CCOCC1.C(N)C1C=CC=CC=1>C1COCC1.CN(C1C=CN=CC=1)C.CCOC(C)=O>[NH2:15][C:10]1([C:13]#[N:14])[CH2:11][CH2:12][N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:9]1

参加物

8

反応物 4

HCID 7504BenzylamineHCID 79724-MethylmorpholineHCID 821294-Nitrophenyl chloroformateHCID 23589510HCID 23589510、化合物

生成物 1

HCID 220633693-Amino-1-benzylpyrrolidine-3-carbonitrile収率 89.4%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 2-hydroxy-4-methyl-pentanoic acid (1-benzyl-3-cyano-pyrrolidin-3-yl)-amide (0.315 g, 1.0 mmol) in dry THF (27 mL) was added DMAP (0.171 g, 1.4 mmol), p-nitrophenyl chloroformate (0.221 g, 1.1 mmol), and N-methylmorpholine (0. 121 mL, 1.1 mmol). The resulting mixture was allowed to stir overnight (20 h) under argon at room temperature, then treated with benzylamine (0.150 g, 1.4 mmol) and allowed to stir overnight (24 h). When the reaction was complete, the mixture was diluted with EtOAc (50 mL), then washed sequentially with saturated aq. NaHCO3 (50 mL), water and brine, dried over Na2SO4, filtered and concentrated to give 0.180 g (40% yield ) of the desired product after purification by prep-HPLC; 1H NMR (CDCl3) 7.25 (10H, m), 6.25 (1H, s), 5.4-5.1 (2H, m), 4.45 (2H, m), 3.65 (2H, m), 3.1-3.0 (1H, m), 2.98-2.57 (5H, m), 2.16 (1H, m), 1.73 (2H, m), 0.9 (6H, m). MS, m/z 449=M+1.

後処理

  1. stirringto stir overnight (24 h)
  2. washwashed sequentially with saturated aq. NaHCO3 (50 mL), water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-3db83ddcbd7f4cd68ecbead9042102dd
出典データセット
uspto-grants-2006_01
特許番号
US06982263B2

反応ノート

読み込み中…