Trifluoroacetic acid → (R)-3-(4-chloro-benzyloxy)-pyrrolidine

HRID 557056Notes

Reaction equation

HRID 557056 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][C@@H:10]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:14][O:13][C@@H:10]2[CH2:11][CH2:12][NH:8][CH2:9]2)=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66757611(R)-3-(4-chlorobenzyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 53765332(R)-3-(4-chloro-benzyloxy)-pyrrolidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (R)-3-(4-chlorobenzyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester (0.88 mmol) in dichloromethane cooled at 0° C. was treated with trifluoroacetic acid (20%) and warmed to room temperature and stirred for 2 h. The reaction mixture was concentrated in vacuo, diluted with ethyl acetate and free based with 10% aqueous sodium bicarbonate. The combined organics were dried over sodium sulfate. The product was used without any further purification. ESI-MS m/z: 211 (M+1), UV retention time: 0.97 min.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additiondiluted with ethyl acetate
  3. dry with materialThe combined organics were dried over sodium sulfate
  4. customThe product was used without any further purification

Sources & evidence

ORD record
ord-510b5c69741d4978a547f956c8cc9052
Source dataset
uspto-grants-2011_11
Patent number
US08058287B2

Reaction notes

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