Isopropanol → Propan-2-yl Pyrrolidine-2-carboxylate

HRID 926398Notes

Reaction equation

HRID 926398 reaction equation
C1([C@H](NC([C:13]2[CH:14]=[C:15]([C:22](N3CCC[C@@H]3C(O)=O)=[O:23])[N:16]3CCOC[C:17]=23)=O)CC)C=CC=CC=1.[CH:32]([OH:35])([CH3:34])[CH3:33]>Cl>[CH:32]([O:35][C:22]([CH:15]1[CH2:14][CH2:13][CH2:17][NH:16]1)=[O:23])([CH3:34])[CH3:33]

Participants

4

Reactant 2

HCID 3776IsopropanolHCID 89726399(R)-1-[8-((R)-1-phenyl-propylcarbamoyl)-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-6-carbonyl]-pyrrolidine-2-carboxylic acid

Product 1

HCID 11051913Propan-2-yl Pyrrolidine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidCatalyst

Procedure

A solution of (R)-1-[8-((R)-1-phenyl-propylcarbamoyl)-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-6-carbonyl]-pyrrolidine-2-carboxylic acid in isopropanol and 2 drops of concentrated aqueous hydrochloric acid was heated to reflux overnight. Solvents were evaporated. The residue was dissolved in a small amount of acetonitrile, excess water was added and the solution was freeze-dried to give 27 mg (49%) of (R)-1-[84(R)-1-phenyl-propylcarbamoyl)-3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-6-carbonyl]-pyrrolidine-2-carboxylic acid isopropyl ester. LC/MS (method 4): Rt=1.27 min; m/z=468.35 (M+H+).

Workup

  1. temperatureto reflux overnight
  2. customSolvents were evaporated
  3. dissolutionThe residue was dissolved in a small amount of acetonitrile, excess water
  4. additionwas added
  5. customthe solution was freeze-dried

Sources & evidence

ORD record
ord-d1c8c5826dff4682afb76d29226e139c
Source dataset
uspto-grants-2016_03
Patent number
US09284333B2

Reaction notes

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