Benzylamine → (S)-N-benzyl-1-(2,2-dimethyl-1,3-dioxolan-4-yl)methanamine

HRID 533191

반응식

HRID 533191 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>CC#N>[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

4

반응물 2

HCID 7504BenzylamineHCID 15570842HCID 15570842, 화합물

생성물 1

HCID 11042283(S)-N-benzyl-1-(2,2-dimethyl-1,3-dioxolan-4-yl)methanamine수율 76%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

The title compound was prepared in the same way as described by M. Lemaire, F. Posada, J.-G. Gourcy and G. Jeminet, Synlett, 1995, 627. A solution of (R)-(2,2-dimethyl-1,3-dioxolan-4-yl)methyl methanesulfonate (3.9 g, 18.55 mmol) and benzylamine (8.10 ml, 74.2 mmol) was refluxed in CH3CN (50 ml) for 48 h. 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 (S)—N-benzyl-1-(2,2-dimethyl-1,3-dioxolan-4-yl)methanamine (3.1 g, 14.01 mmol, 76% yield) as a yellow oil. [α]D21 +4.3 (c, 0.69, CHCl3). The 1H NMR and 13C NMR were identical to that of compound 3.2.

후처리

  1. customThe title compound was prepared in the same way
  2. customThe solvent was evaporated
  3. dissolutionthe residue dissolved in EtOAc
  4. washwashed with aqueous sat. NaHCO3
  5. customdried
  6. customthe solvent evaporated
  7. customThe residue was chromatographed (EtOAc-hex, 6:4

출처 및 근거

ORD 기록
ord-0b8544a54aa94a45922017aa49d330a9
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853224B2

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