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

HRID 1609826노트

반응식

HRID 1609826 반응식
[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

참가 물질

8

반응물 4

HCID 7504BenzylamineHCID 79724-MethylmorpholineHCID 821294-Nitrophenyl chloroformateHCID 23589510HCID 23589510, 화합물

생성물 1

HCID 220633693-Amino-1-benzylpyrrolidine-3-carbonitrile수율 89.4%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3db83ddcbd7f4cd68ecbead9042102dd
출처 데이터셋
uspto-grants-2006_01
특허 번호
US06982263B2

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