Diisopropylethylamine → HCID 58046461, compound

HRID 1891323Notes

Reaction equation

HRID 1891323 reaction equation
C([N:8]1[CH2:12][CH:11]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[C:10]([CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][N:24]=2)([CH3:20])[CH2:9]1)C1C=CC=CC=1.ClC(OC(Cl)C)=O.CCN(C(C)C)C(C)C>C1(C)C=CC=CC=1>[Cl:29][C:26]1[CH:27]=[CH:28][C:23]([O:22][CH2:21][C:10]2([CH3:20])[CH:11]([C:13]3[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=3)[CH2:12][NH:8][CH2:9]2)=[N:24][CH:25]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 5213051-Chloroethyl chloroformateHCID 67016478HCID 67016478, compound

Product 1

HCID 58046461HCID 58046461, compoundYield 107.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of 2-[(3RS,4RS)-1-benzyl-4-(4-chloro-phenyl)-3-methyl-pyrrolidin-3-ylmethoxy]-5-chloro-pyridine (0.70 g, 1.64 mmol) in toluene (10 mL) at RT was added 1-chloroethyl chloroformate (0.229 mL, 2.12 mmol) and iPr2NEt (0.36 mL, 2.12 mmol). After 3 hours all volatiles were removed under high vacuum and the residue was dissolved in MeOH (10 mL). The reaction mixture was stirred at RT for 2 hours, and then concentrated under high vacuum. Column chromatography (SiO2, CH2Cl2/MeOH, 9:1) afforded 595 mg (97%) of the title product as white foam. ES-MS m/e: 337.1 (M+H+).

Workup

  1. customAfter 3 hours all volatiles were removed under high vacuum
  2. dissolutionthe residue was dissolved in MeOH (10 mL)
  3. concentrationconcentrated under high vacuum

Sources & evidence

ORD record
ord-c7730733fdbf4c90a81abe2ff8b8a1ef
Source dataset
uspto-grants-2013_08
Patent number
US08507535B2

Reaction notes

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