Hydrochloric Acid → (3R)-3-acetoxy-1-(tert-butoxycarbonyl)-L-proline

HRID 1424208Notes

Reaction equation

HRID 1424208 reaction equation
N1C=CC=CC=1.[C:7](OC(=O)C)(=[O:9])[CH3:8].[C:14]([N:21]1[CH2:28][CH2:27][C@@H:26]([OH:29])[C@H:22]1[C:23]([OH:25])=[O:24])([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].Cl>O>[C:7]([O:29][C@@H:26]1[CH2:27][CH2:28][N:21]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C@@H:22]1[C:23]([OH:25])=[O:24])(=[O:9])[CH3:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 11096439(2S,3R)-3-Hydroxypyrrolidine-2-carboxylic acid, N-BOC protected

Product 1

HCID 86699073(3R)-3-acetoxy-1-(tert-butoxycarbonyl)-L-prolineYield 78%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Pyridine (5 mL) and acetic anhydride (2 mL) were added to N-boc-cis-3-hydroxy-L-proline (400 mg, 1.73 mmol) and the reaction was stirred for 4 hours at room temperature. The reaction was diluted with water, acidified with 1N HCl and extracted with EtOAc. The organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford the title compound (370 mg, 78%).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0c43d5cde72245ed8f85af6c515c04db
Source dataset
uspto-grants-2015_01
Patent number
US08927587B2

Reaction notes

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