Hydrochloric Acid → HCID 11773132, compound

HRID 2113501Notes

Reaction equation

HRID 2113501 reaction equation
[OH:1][C@H:2]1[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@H:4]([CH2:14][O:15][Si](C(C)(C)C)(C)C)[CH2:3]1.[C:23]1([CH3:33])[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1.Cl.CC1C=CC(S(O)(=O)=O)=CC=1.O.C([O-])(O)=O.[Na+]>N1C=CC=CC=1>[OH:15][CH2:14][C@@H:4]1[CH2:3][C@@H:2]([O:1][S:29]([C:26]2[CH:27]=[CH:28][C:23]([CH3:33])=[CH:24][CH:25]=2)(=[O:31])=[O:30])[CH2:6][N:5]1[C:7]([O:9][C:10]([CH3:11])([CH3:12])[CH3:13])=[O:8]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 11174939Tert-butyl (2S,4R)-2-(((tert-butyldimethylsilyl)oxy)methyl)-4-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 11773132HCID 11773132, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Intermediate Compound 89A (3.41 g, 10.3 mmol) was dissolved in anhydrous pyridine (30.0 mL) and cooled to 0° C. p-Toluenesulfonylchloride (5.89 g, 30.9 mmol) was then added in portions over a 10 minute period. The flask was then placed in a refrigerator at 4° C. for 48 h. The resulting solution was poured into 1 N HCl (300 mL), extracted with methylene chloride (3×200 mL) and the organics were dried over anhydrous sodium sulfate. The crude tosylate intermediate was dissolved in THF (50 mL), to which was added H2O (0.5 mL) followed by pTSA-H2O (1.03 mmol). Once the reaction was complete as determined by TLC, the mixture was poured into saturated aqueous NaHCO3 (150 mL) and extracted with methylene chloride (3×50 mL). The combined organics were dried over sodium sulfate. The crude alcohol was purified by flash chromatography on SiO2 eluting with acetone/chloroform (0-5-10% acetone) to give 2.71 g (71% for 2-steps) of intermediate Compound 89B as a clear oil.

Workup

  1. additionwas then added in portions over a 10 minute period
  2. extractionextracted with methylene chloride (3×200 mL)
  3. dry with materialthe organics were dried over anhydrous sodium sulfate
  4. dissolutionThe crude tosylate intermediate was dissolved in THF (50 mL), to which
  5. additionwas added H2O (0.5 mL)
  6. extractionextracted with methylene chloride (3×50 mL)
  7. dry with materialThe combined organics were dried over sodium sulfate
  8. customThe crude alcohol was purified by flash chromatography on SiO2 eluting with acetone/chloroform (0-5-10% acetone)

Sources & evidence

ORD record
ord-5ae5e973c8554ea382b9ef95ed10d8dc
Source dataset
uspto-grants-2008_10
Patent number
US07432267B2

Reaction notes

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