Diisopropylethylamine → (3S)-(1-(3,4-difluorobenzyl)pyrrolidin-3-yl)carbamic acid tert-butyl ester

HRID 2247522Notes

Reaction equation

HRID 2247522 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:13][CH2:12][NH:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=1[F:23])[CH2:18]Br.C(N(C(C)C)CC)(C)C.O.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:7])[NH:8][C@H:9]1[CH2:13][CH2:12][N:11]([CH2:18][C:17]2[CH:20]=[CH:21][C:22]([F:23])=[C:15]([F:14])[CH:16]=2)[CH2:10]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 5814364-(Bromomethyl)-1,2-difluorobenzeneHCID 1514396(3S)-(-)-3-(tert-Butoxycarbonylamino)pyrrolidineHCID 86585896Sodium bicarbonate water

Product 1

HCID 66961515(3S)-(1-(3,4-difluorobenzyl)pyrrolidin-3-yl)carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a methylene chloride (10 mL) solution of (3S)-3-(tert-butoxycarbonylamino)pyrrolidine (916 mg), 3,4-difluorobenzylbromide (0.7 mL) and IPEA (2.2 mL) were added one by one, and the reaction solution was agitated at room temperature for 20 hours. A saturated sodium bicarbonate water was added to the reaction solution after the reaction ended, and the organic layer was partitioned. It was dried over anhydrous magnesium sulfate and the obtained organic layer was concentrated under reduced pressure. 1.55 g of the title compound was obtained by purifying the residue by silica gel chromatography (elution solvent: heptane:ethyl acetate=1:1). The physical properties of the compound are as follows.

Workup

  1. customthe organic layer was partitioned
  2. dry with materialIt was dried over anhydrous magnesium sulfate
  3. concentrationthe obtained organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-735d59deac714328b3139566ead15cc2
Source dataset
uspto-grants-2010_03
Patent number
US07687640B2

Reaction notes

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