Diisopropylethylamine → HCID 68089233, compound

HRID 1918229Notes

Reaction equation

HRID 1918229 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9](=[O:32])[N:10]([C@:12]2([CH3:31])[C@@H:16]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)[CH2:15][N:14](CC3C=CC=CC=3)[CH2:13]2)[CH3:11])=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.ClC(OC(Cl)C)=O>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9](=[O:32])[N:10]([C@:12]2([CH3:31])[C@@H:16]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)[CH2:15][NH:14][CH2:13]2)[CH3:11])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 5213051-Chloroethyl chloroformateHCID 68089489HCID 68089489, compound

Product 1

HCID 68089233HCID 68089233, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 1.65 g (3.64 mmol) rac-[(3R,4S)-1-Benzyl-4-(4-chloro-phenyl)-3-methyl-pyrrolidin-3-yl]-methyl-carbamic acid 4-fluoro-phenyl ester, 0.75 g (5.83 mmol) DIPEA and 0.78 g (5.46 mmol) 1-chloroethyl chloroformate in 40 mL toluene was stirred at room temperature and evaporated to dryness. The residue was taken up in 40 mL methanol and stirred for 2 h at room temperature and evaporated to dryness to yield the crude title compound which was used without further purification in the consecutive step.

Workup

  1. customevaporated to dryness
  2. stirringstirred for 2 h at room temperature
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-cddd492a950f4ee5a1aa8cef15742961
Source dataset
uspto-grants-2013_12
Patent number
US08618303B2

Reaction notes

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