Hydrochloric Acid → HCID 58104601, compound

HRID 1671374Notes

Reaction equation

HRID 1671374 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][C@H:10]([C@@H:13]([O:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=2[Cl:24])[CH2:14][CH3:15])[CH2:9]1)=O)(C)(C)C.Cl.CCO>>[Cl:24][C:18]1[CH:19]=[C:20]([Cl:23])[CH:21]=[CH:22][C:17]=1[O:16][C@H:13]([C@H:10]1[CH2:11][CH2:12][NH:8][CH2:9]1)[CH2:14][CH3:15]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 66889301HCID 66889301, compound

Product 1

HCID 58104601HCID 58104601, compound

Procedure

60% NaH in mineral oil (60:40, NaH:mineral oil, 10 mg, 260 μmmol) was slowly added to a mixture of (S)-3-(S)-1-hydroxypropyl)pyrrolidine-1-carboxylic acid t-butyl ester (50 mg, 0.2 mmol, 1 eq.) in DMF (680 μL, 8.7 mmol). The resulting mixture was stirred for 15 minutes, at room temperature. 2,4-Dichloro-1-fluorobenzene (76 μL, 3 eq.) was added and the mixture was heated at 90° C. for 3 hours. The reaction was quenched with MeOH (1 mL). DMF and MeOH was removed under reduced pressure, leaving the BOC-protected intermediate, (S)-3-[(S)-1-(2,4-dichlorophenoxy)propyl]pyrrolidine-1-carboxylic acid t-butyl ester. Deprotection was carried out using 1.25 M HCl in EtOH (1.7 mL, 2.2 mmol). The mixture was stirred overnight at room temperature. The product was then purified by preparative HPLC to yield the title compound as a mono-TFA salt (41.5 mg). MS m/z: [M+H]+ calcd for C13H17Cl2NO, 274.07; found 274.0.

Workup

  1. customThe product was then purified by preparative HPLC

Sources & evidence

ORD record
ord-f11ed634310a4dccad7b67aafcae67a7
Source dataset
uspto-grants-2011_08
Patent number
US07994209B2

Reaction notes

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