Hydrochloric Acid → HCID 3687912, compound

HRID 1162732Notes

Reaction equation

HRID 1162732 reaction equation
C([O:3][C:4]([CH:6]1[CH:10]([C:11]([F:14])([F:13])[F:12])[CH2:9][N:8]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:7]1)=[O:5])C.[Li+].[OH-].Cl>C1COCC1.O.C(Cl)Cl>[C:18]([O:17][C:15]([N:8]1[CH2:9][CH:10]([C:11]([F:14])([F:12])[F:13])[CH:6]([C:4]([OH:5])=[O:3])[CH2:7]1)=[O:16])([CH3:21])([CH3:19])[CH3:20]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 68646726HCID 68646726, compound

Product 1

HCID 3687912HCID 3687912, compoundYield 65.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
25 °C

Procedure

107.2 (3RS,4SR)-4-Trifluoromethyl-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester (9.76 g) was dissolved in THF/water (1:1 10 ml) and LiOH (0.826 g) was added to the emulsion. The mixture was stirred for 18 h at 25° C. The reaction mixture was then diluted with CH2Cl2 (50 ml) and treated with HCl (1N, 20 ml). The aqueous phase was extracted twice with CH2Cl2 (20 ml) and the combined organic layers were dried over Na2SO4, filtered and evaporated to dryness to yield (3RS,4SR)-4-trifluoromethyl-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester (5.8 g) as light yellow solid. MS 284.3 ([M+H]+).

Workup

  1. extractionThe aqueous phase was extracted twice with CH2Cl2 (20 ml)
  2. dry with materialthe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-dc55f9d456024f958e4f95c42e2a8077
Source dataset
uspto-grants-2010_10
Patent number
US07820699B2

Reaction notes

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