Hydrogen Bromide → 4-methyl-2-[(2R)-pyrrolidin-2-yl]-1,3-oxazole

HRID 2071113Notes

Reaction equation

HRID 2071113 reaction equation
Br.[CH3:2][C:3]1[N:4]=[C:5]([C@H:8]2[CH2:12][CH2:11][CH2:10][N:9]2C(OCC2C=CC=CC=2)=O)[O:6][CH:7]=1.CCOCC>CC(O)=O>[CH3:2][C:3]1[N:4]=[C:5]([C@H:8]2[CH2:12][CH2:11][CH2:10][NH:9]2)[O:6][CH:7]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 3283Diethyl EtherHCID 86647436(R)-benzyl 2-(4-methyloxazol-2-yl)pyrrolidine-1-carboxylate

Product 1

HCID 595708394-methyl-2-[(2R)-pyrrolidin-2-yl]-1,3-oxazole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

HBr in AcOH (60 mL) was added to (R)-benzyl 2-(4-methyloxazol-2-yl)pyrrolidine-1-carboxylate (neat) at room temperature. After 1 h, ether (20 mL) was added slowly with vigorous string. Stirring was continued for 10 min and allowed to settle for 5-10 min. The supernatant was decanted. This process was repeated 3-4 times until the supernatant was colourless. The semi-solid was dissolved in water (50 mL) and brought to pH ˜8 with 1N LiOH and extracted with 5% MeoH/95% CHCl3

Workup

  1. waitwas continued for 10 min
  2. waitto settle for 5-10 min
  3. customThe supernatant was decanted
  4. dissolutionThe semi-solid was dissolved in water (50 mL)
  5. extractionextracted with 5% MeoH/95% CHCl3

Sources & evidence

ORD record
ord-7d97890507714da382f4cc0677372f47
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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