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

HRID 390071
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HRID 390071 반응식
[CH3:1][C:2]1([CH3:9])[O:6][C@@H:5]([CH2:7]O)[CH2:4][O:3]1.[CH3:10][S:11]([O:14][CH2:15][C@H:16]1[CH2:20][O:19][C:18]([CH3:22])([CH3:21])[O:17]1)(=[O:13])=[O:12].[CH2:23]([NH2:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CC#N>[CH3:10][S:11]([O:14][CH2:15][C@H:16]1[CH2:20][O:19][C:18]([CH3:22])([CH3:21])[O:17]1)(=[O:12])=[O:13].[CH2:23]([NH:30][CH2:7][C@H:5]1[CH2:4][O:3][C:2]([CH3:1])([CH3:9])[O:6]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 7504BenzylamineHCID 736057(+)-SolketalHCID 15570842Methanesulfonic acid [(R)-2,2-dimethyl-[1,3]dioxolan-4-yl]methyl ester

생성물 2

HCID 11042283(S)-N-benzyl-1-(2,2-dimethyl-1,3-dioxolan-4-yl)methanamine수율 76%HCID 15570842Methanesulfonic acid [(R)-2,2-dimethyl-[1,3]dioxolan-4-yl]methyl ester

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

(R)-(2,2-Dimethyl-1,3-dioxolan-4-yl)methyl methanesulfonate was prepared from (S)-(2,2-dimethyl-1,3-dioxolan-4-yl)methanol (Sigma-Aldrich, 99% ee) by a known literature procedure (H. S. Kim, D. Barak, T. K. Harden, J. L. Boyer and K. A. Jacobson, J. Med. Chem., 2001, 44, 3092). 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.

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-2dafa71afaf54e4bb5b7cb2364c7cbdb
출처 데이터셋
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08383636B2

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