p-Toluenesulfonic acid → tert-butyl (S)-1-hydroxy-3-((R)-1-methyl-6-oxopiperidin-3-yl)propan-2-ylcarbamate

HRID 451813Notes

Reaction equation

HRID 451813 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][C:18](=[O:21])[N:17]([CH3:22])[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][C:18](=[O:21])[N:17]([CH3:22])[CH2:16]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 90495Di-tert-butyl dicarbonateHCID 59201489(S)-tert-butyl 2,2-dimethyl-4-(((R)-1-methyl-6-oxopiperidin-3-yl)methyl)oxazolidine-3-carboxylate

Product 1

HCID 59201482tert-butyl (S)-1-hydroxy-3-((R)-1-methyl-6-oxopiperidin-3-yl)propan-2-ylcarbamate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (S)-tert-butyl 2,2-dimethyl-4-(((R)-1-methyl-6-oxopiperidin-3-yl)methyl)oxazolidine-3-carboxylate (230 mg, 0.70 mmol) in MeOH (10 mL) was added p-TSA (30 mg, 0.17 mmol) and stirred at rt overnight. TEA (1 mL) was added, followed by Boc2O (30 mg). The reaction mixture was stirred for another 30 min. The solvent was removed under vacuum to give crude product tert-butyl (S)-1-hydroxy-3-((R)-1-methyl-6-oxopiperidin-3-yl)propan-2-ylcarbamate, which was used for next step without further purification. MS ESI +ve m/z 287 (M+H).

Workup

  1. stirringThe reaction mixture was stirred for another 30 min
  2. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-7a1f4d0b0f414a408a58104c0536043a
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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