Potassium Phosphate, Tribasic → {1-[3-(3-Dimethylamino-pyrrolidin-1-yl)-phenyl]-ethyl}-carbamic acid tert-butyl ester

HRID 857019Notes

Reaction equation

HRID 857019 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][C@H:8]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12](Br)[CH:11]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2].[CH3:18][N:19]([CH3:25])[C@@H:20]1[CH2:24][CH2:23][NH:22][CH2:21]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>COCCOC.C(Cl)Cl.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:1]([O:5][C:6](=[O:17])[NH:7][CH:8]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N:22]2[CH2:23][CH2:24][CH:20]([N:19]([CH3:25])[CH3:18])[CH2:21]2)[CH:11]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 2758521(3R)-(+)-3-(Dimethylamino)pyrrolidineHCID 56971804(S)-N-Boc-1-(3-bromophenyl)ethylamine

Product 1

HCID 69588726{1-[3-(3-Dimethylamino-pyrrolidin-1-yl)-phenyl]-ethyl}-carbamic acid tert-butyl esterYield 27%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of (S )[1-(3-bromo-phenyl)-ethyl]-carbamic acid tert-butyl ester (6 g), (3R)-3-(dimethylamino)-pyrrolidine (4.56 g), Pd2(dba)3 (1.83 g), di-t-butyl-biphenylphosphine (600 mg), K3PO4 (8.48 g) in DME (40 mL) was stirred at reflux for 16 h. The reaction mixture was cooled down to room temperature, diluted with methylene chloride, and filtered. The filtrated was evaporated in vacuo, and the crude product was purified by Flash Chromatography using Biotage eluting with 20% MeOH in ethyl acetate to give the title compound (1.8 g) as an oil.

Workup

  1. temperatureat reflux for 16 h
  2. filtrationfiltered
  3. customThe filtrated was evaporated in vacuo
  4. customthe crude product was purified by Flash Chromatography
  5. washeluting with 20% MeOH in ethyl acetate

Sources & evidence

ORD record
ord-25c8f9ac53e244bba0ba6badd5929881
Source dataset
uspto-grants-2006_12
Patent number
US07144881B2

Reaction notes

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