Vinyl Chloride → HCID 9838506, compound

HRID 2258573Notes

Reaction equation

HRID 2258573 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH2:9][CH:10]2[CH2:13][CH2:14][NH2:15])=[CH:5][CH:4]=1.C(O)(=O)[C@H]([C@@H](C(O)=O)O)O.C=CCl.OP([O-])(O)=O.[K+].[CH3:35][O:36][CH2:37][C:38](Cl)=[O:39].[K+].[Br-]>C(Cl)(Cl)Cl.C(#N)C>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH2:9][CH:10]2[CH2:13][CH2:14][NH:15][C:38](=[O:39])[CH2:37][O:36][CH3:35])=[CH:5][CH:4]=1

Participants

9

Reactant 6

HCID 6338Vinyl ChlorideHCID 96623Methoxyacetyl chlorideHCID 253877Potassium BromideHCID 439655D-Tartaric acidHCID 516951Monobasic potassium phosphateHCID 21996472HCID 21996472, compound

Product 1

HCID 9838506HCID 9838506, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6342AcetonitrileSolvent

Procedure

N-[2-(1,2,3,4-tetrahydro-7-methoxy naphthalen-1-yl)ethyl]amine was resolved according to the procedure described using D-tartaric acid and shown to have an enantomeric excess of 92% by HPLC analysis. The HPLC analyses were performed on a Ultron ES-OVM, 150×4.6 mm column using an isocratic mobile phase at 95/5 (A/B) where A is 20 mM KH2PO4, pH=3.0 and B is acetonitrile. This amine was converted into the amide according to General Procedure A using methoxyacetyl chloride. The final product was purified by recrystallization from EtOAc/hexane to give a white solid. m.p.=61°-63° C.; 1H NMR (300 MHz, CDCl3) δ6.96 (d, J=8 Hz, 1H), 6.67 (s, 1H), 6.65 (m, 1H), 6.51 (bs, 1H), 3.86 (s, 2H), 3.75 (s, 3H), 3.42 (m, 2H), 3.38 (s, 3H), 2.78 (m, 1H), 2.66 (bm, 2H), 1.97-1.76 (bm, 4H), 1.68-1.65 (m, 2H); 13C NMR (75 MHz, CDCl3) δ169.42, 157.55, 141.23, 130.01, 129.21, 113.34, 111.80, 71.99, 59.15, 55.28, 36.93, 36.45, 35.64, 28.72, 27.51, 20.00; IR (KBr) 1656 cm-1 ; MS (DCI) m/e 278 (MH); Analysis calc'd for C16H23N1O3 : C, 69.29; H, 8.36; N, 5.05; found: C, 69.15; H, 8.33; N, 4.89; [α] (25° C., 589 nm, CHCl3)=-8.33.

Workup

  1. customThe final product was purified by recrystallization from EtOAc/hexane
  2. customto give a white solid

Sources & evidence

ORD record
ord-5037121c05174907b83ff6864f26a0be
Source dataset
uspto-grants-1997_08
Patent number
US05661186

Reaction notes

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