1,4-Dioxane hydrochloride → HCID 117839372, compound

HRID 1477608Notes

Reaction equation

HRID 1477608 reaction equation
[CH2:1]([N:8]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C@H:9]1[C@H:13]([OH:14])[CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.O1CCOCC1>>[CH2:22]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C@@H:9]1[CH2:10][NH:11][CH2:12][C@H:13]1[OH:14])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

3

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 131736489HCID 131736489, compound

Product 1

HCID 117839372HCID 117839372, compoundYield 100.4%

Procedure

To tert-butyl (3R,4R)-3-(dibenzylamino)-4-hydroxy-pyrrolidine-1-carboxylate (350 mg, 0.91 mmol) synthesized in Reference Synthesis Example 71, 4 M hydrogen chloride/1,4-dioxane solution (3 mL) was added and the resultant solution was stirred at room temperature. The reaction solution was concentrated under reduced pressure and chloroform was added to the obtained residue, followed by washing the resultant mixture with saturated sodium bicarbonate aqueous solution. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain a crude product (258 mg) of the title compound.

Workup

  1. additionwas added
  2. concentrationThe reaction solution was concentrated under reduced pressure and chloroform
  3. additionwas added to the obtained residue
  4. washby washing the resultant mixture with saturated sodium bicarbonate aqueous solution
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6bc8577c3795459ba3373fa9dd0e94cd
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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