Thionyl Chloride → HCID 59533567, compound

HRID 1430087Notes

Reaction equation

HRID 1430087 reaction equation
[CH2:1]([N:8]1[CH2:13][C@H:12]([CH2:14]O)[C@H:11]2[O:16][C@@:17]([O:24][CH3:25])([CH3:23])[C@:18]([O:21][CH3:22])([CH3:20])[O:19][C@@H:10]2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:28])=O>C(Cl)(Cl)Cl>[CH2:1]([N:8]1[CH2:13][C@H:12]([CH2:14][Cl:28])[C@H:11]2[O:16][C@@:17]([O:24][CH3:25])([CH3:23])[C@:18]([O:21][CH3:22])([CH3:20])[O:19][C@@H:10]2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 59533569HCID 59533569, compound

Product 1

HCID 59533567HCID 59533567, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of ((2S,3S,4aR,8R,8aR)-6-benzyl-2,3-dimethoxy-2,3-dimethyloctahydro-[1,4]dioxino[2,3-c]pyridine-8-yl)methanol (1) (2.5 g, 7.1 mmol) in chloroform (35 mL) was added thionyl chloride (1.3 mL, 18 mmol). The resulting mixture was heated at reflux for 4-8 hours until reaction was judged complete by TLC (98:2 CH2Cl2/2-PrOH). Solvent and excess reagent were evaporated in vacuo and the residue was chromatographed (98:2 CH2Cl2/2-PrOH) to give the title compound (2.2 g, 85%). Product was characterized via HPLC/MS (MH+=369). Purity was judged as >95%.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 4-8 hours until reaction
  3. customSolvent and excess reagent were evaporated in vacuo
  4. customthe residue was chromatographed (98:2 CH2Cl2/2-PrOH)

Sources & evidence

ORD record
ord-fb81c59a7ab144c1b4bcd34a3bb2966d
Source dataset
uspto-grants-2015_01
Patent number
US08940766B2

Reaction notes

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