(2S,4S)-4-(3-chloro-phenoxymethyl)-pyrrolidine-1,2-dicarboxylic acid di-tert-butyl ester → (2S,4S)-4-(3-chloro-phenoxymethyl)-pyrrolidine-2-carboxylic acid

HRID 1442955Notes

Reaction equation

HRID 1442955 reaction equation
C(OC([N:8]1[CH2:12][C@@H:11]([CH2:13][O:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=2)[CH2:10][C@H:9]1[C:22]([O:24]C(C)(C)C)=[O:23])=O)(C)(C)C>Cl.O1CCOCC1>[Cl:21][C:17]1[CH:16]=[C:15]([CH:20]=[CH:19][CH:18]=1)[O:14][CH2:13][C@@H:11]1[CH2:12][NH:8][C@H:9]([C:22]([OH:24])=[O:23])[CH2:10]1

Participants

4

Reactant 1

HCID 59166773(2S,4S)-4-(3-chloro-phenoxymethyl)-pyrrolidine-1,2-dicarboxylic acid di-tert-butyl ester

Product 1

HCID 54580790(2S,4S)-4-(3-chloro-phenoxymethyl)-pyrrolidine-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

(2S,4S)-4-(3-chloro-phenoxymethyl)-pyrrolidine-1,2-dicarboxylic acid di-tert-butyl ester (Preparation 46, 67 mg, 0.16 mmol) was dissolved in a solution of anhydrous hydrogen chloride in dioxane (4M, 5 ml) and stirred for 18 hours at room temperature. The solvent was removed under reduced pressure and the residue triturated with ethyl acetate to give the title compound as a white solid hydrochloride salt (13 mg, 27%)

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue triturated with ethyl acetate

Sources & evidence

ORD record
ord-8a83deba1f84411ca6fca5abf1264267
Source dataset
uspto-grants-2010_02
Patent number
US07659305B2

Reaction notes

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