p-Toluenesulfonic acid → tert-Butyl ((S)-1-hydroxy-3-((R)-tetrahydro-2H-pyran-3-yl)propan-2-yl)carbamate

HRID 218420Notes

Reaction equation

HRID 218420 reaction equation
CC1(C)[N:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@@H:5]([CH2:14][C@H:15]2[CH2:20][CH2:19][CH2:18][O:17][CH2:16]2)[CH2:4][O:3]1.CC1C=CC(S(O)(=O)=O)=CC=1.CC(OC(OC(OC(C)(C)C)=O)=O)(C)C>CO>[OH:3][CH2:4][C@@H:5]([NH:6][C:7](=[O:8])[O:9][C:10]([CH3:12])([CH3:11])[CH3:13])[CH2:14][C@H:15]1[CH2:20][CH2:19][CH2:18][O:17][CH2:16]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 90495Di-tert-butyl dicarbonateHCID 58011520(S)-tert-Butyl 2,2-dimethyl-4-(((R)-tetrahydro-2H-pyran-3-yl)methyl)oxazolidine-3-carboxylate

Product 1

HCID 58011540tert-Butyl ((S)-1-hydroxy-3-((R)-tetrahydro-2H-pyran-3-yl)propan-2-yl)carbamate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (S)-tert-butyl 2,2-dimethyl-4-(((R)-tetrahydro-2H-pyran-3-yl)methyl)oxazolidine-3-carboxylate (643 mg, 2.15 mmol) in MeOH (10 mL) was added p-TSA (37 mg, 0.22 mmol), then the solution was stirred at rt for 12 hr. TEA (2 mL) was added, followed by Boc2O (46 mg, 0.21 mmol). After the addition the reaction solution was stirred for another 30 min. The organic solvent was removed under reduced pressure to give the crude product tert-butyl (S)-1-hydroxy-3-((R)-tetrahydro-2H-pyran-3-yl)propan-2-ylcarbamate. It was used in the next step without further purification. MS ESI+ve m/z 260 (M+1).

Workup

  1. additionAfter the addition the reaction solution
  2. stirringwas stirred for another 30 min
  3. customThe organic solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-02d7ac3772a544138cd8a819079db831
Source dataset
uspto-grants-2012_06
Patent number
US08198453B2

Reaction notes

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