Benzylamine → HCID 25223591, 화합물

HRID 533185

반응식

HRID 533185 반응식
CS(O[CH2:6][C@@H:7]1[CH2:11][O:10][C:9]([CH3:13])([CH3:12])[O:8]1)(=O)=O.[CH2:14]([NH2:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CCOC(C)=O.C1C=C2C(C(O)(O)C(=O)C2=CC=1)=O>CC#N.[O-][Mo]([O-])(=O)=O>[CH2:14]([NH:21][CH2:6][C@@H:7]1[CH2:11][O:10][C:9]([CH3:12])([CH3:13])[O:8]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

참가 물질

7

반응물 4

HCID 7504BenzylamineHCID 8857Ethyl AcetateHCID 10236NinhydrinHCID 24903512[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl methanesulfonate

생성물 1

HCID 25223591HCID 25223591, 화합물수율 81.1%

시약·촉매·용매 2

HCID 24621Molybdate ion촉매HCID 6342Acetonitrile용매

실험 절차

The title compound was prepared in the same way as that method described for preparing the (S)-enantiomer (M. Lemaire, F. Posada, J.-G. Gourcy and G. Jeminet, Synlett, 1995, 627). A solution of (S)-(2,2-dimethyl-1,3-dioxolan-4-yl)methyl methanesulfonate (3.0 g, 14.27 mmol) and benzylamine (6.23 ml, 57.1 mmol) were refluxed together in CH3CN (38 ml) for 48 h. Tlc (EtOAc-hex 8:2) showed a new product (uv/molybdate or ninhydrin) with Rf ˜0.3 together with a little higher running sm. The solvent was evaporated and the residue dissolved in EtOAc and washed with aqueous sat. NaHCO3, dried and the solvent evaporated. The residue was chromatographed (EtOAc-hex, 6:4 then 8:2) to give (R)—N-benzyl-1-(2,2-dimethyl-1,3-dioxolan-4-yl)methanamine (2.56 g, 11.57 mmol, 81% yield) as a yellow oil. [α]D21 −3.7 (c, 0.885, CHCl3). 1H NMR (CDCl3, 300 MHz), δ ppm, 7.32-7.20 (m, 5H), 4.25, (m, 1H), 4.03 (dd, 1H, J 8.0, 6.4 Hz), 3.82 (s, 2H), 3.68 (dd, 1H, J 8.0, 6.8 Hz), 2.74 (d, 2H, J 5.7 Hz), 1.40 (s, 3H), 1.35 (s, 3H). 13C NMR (CDCl3, 75.5 MHz), δ ppm, 140.6, 128.8, 128.4, 127.3, 109.5, 75.8, 67.9, 54.4, 52.1, 27.3, 25.8.

후처리

  1. customThe title compound was prepared in the same way as that method
  2. customdescribed for preparing the (S)-enantiomer (M. Lemaire, F. Posada, J.-G. Gourcy and G. Jeminet, Synlett, 1995, 627)
  3. customThe solvent was evaporated
  4. dissolutionthe residue dissolved in EtOAc
  5. washwashed with aqueous sat. NaHCO3
  6. customdried
  7. customthe solvent evaporated
  8. customThe residue was chromatographed (EtOAc-hex, 6:4

출처 및 근거

ORD 기록
ord-b5504589053e4655a73fe4a91c83c464
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853224B2

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