Hydrochloric Acid → HCID 69000630, compound

HRID 2103327Notes

Reaction equation

HRID 2103327 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][C@@H:10]([O:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=3)=[CH:16][CH:15]=2)[CH2:9]1)=O)(C)(C)C.Cl>O1CCOCC1>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([O:20][C:17]2[CH:18]=[CH:19][C:14]([O:13][C@@H:10]3[CH2:11][CH2:12][NH:8][CH2:9]3)=[CH:15][CH:16]=2)=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68998471HCID 68998471, compound

Product 1

HCID 69000630HCID 69000630, compoundYield 46.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(R)-3-[4-(4-Chloro-phenoxy)-phenoxy]-pyrrolidine-1-carboxylic acid tert-butyl ester (1 g, 2.56 mmol) was taken into 4N HCl in dioxane (10 mL), and the reaction was run at room temperature for 24 h. The mixture was concentrated to dryness, and the resulting oil was triturated with diethyl ether to obtain the title product (344 mg, 41%); LCMS, m/z 290 (M+1, free amine) 81% pure; 1H NMR (400 MHz, DMSO); δ 2.13-2.16 (m, 2H), 3.24-3.33 (m, 4H), 5.11 (s, 1H), 6.95 (d, J=8.8, 2H), 7.04 (s, 4H), 7.40 (d, J=8.8, 2H), 9.66 (s, 2H).

Workup

  1. concentrationThe mixture was concentrated to dryness
  2. customthe resulting oil was triturated with diethyl ether

Sources & evidence

ORD record
ord-e0859e4ed5cd46d994aad4e38d29751f
Source dataset
uspto-grants-2009_08
Patent number
US07576102B2

Reaction notes

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