Hydrochloric Acid → HCID 54160796, compound

HRID 975663Notes

Reaction equation

HRID 975663 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([O:12][Si](C(C)(C)C)(C)C)[CH2:9][C@H:8]1[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1)=[O:6])[CH:2]=[CH2:3].Cl.C(=O)(O)[O-].[Na+]>C(#N)C.C(OCC)(=O)C>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([OH:12])[CH2:9][C@H:8]1[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1)=[O:6])[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 54143378HCID 54143378, compound

Product 1

HCID 54160796HCID 54160796, compoundYield 72.4%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2R,4R)-1-allyloxycarbonyl-4-t-butyldimethylsilyloxy-2-(2-pyridylmethyl)pyrrolidine (4.88 g) in acetonitrile (50 ml) was added dropwise conc. hydrochloric acid (3.3 ml) at room temperature. The reaction mixture was stirred for 5 hours, then neutralized with saturated aqueous sodium bicarbonate and diluted with ethyl acetate. The organic layer was separated, washed with brine, dried over magnesium sulfate and evaporated under reduced pressure to give (2R,4R)-1-allyloxycarbonyl-4-hydroxy-2-(2-pyridylmethyl) pyrrolidine (2.46 g). On the other hand the aqueous layer was extracted five times with chloroform. The combined chloroform layer was washed with brine, dried over magnesium sulfate and evaporated under reduced pressure to give (2R,4R)-1-allyloxycarbonyl-4-hydroxy-2-(2-pyridylmethyl) pyrrolidine (0.23 g).

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-ba2c9f648b4d4b49b5ffc15e0eb6ede8
Source dataset
uspto-grants-1997_03
Patent number
US05608056

Reaction notes

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