Triethylamine → HCID 64764382, compound

HRID 734838Notes

Reaction equation

HRID 734838 reaction equation
Br[C:2]1[CH:15]=[CH:14][C:5]([O:6][CH2:7][CH2:8][N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)=[C:4]([CH:16]=[CH2:17])[CH:3]=1.C(N(CC)CC)C.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[H][H]>CO.C1CC=CCCC=C1.C1CC=CCCC=C1.[Cl-].[Cl-].[Rh].[Rh]>[CH2:16]([C:4]1[CH:3]=[CH:2][CH:15]=[CH:14][C:5]=1[O:6][CH2:7][CH2:8][N:9]1[CH2:10][CH2:11][CH2:12][CH2:13]1)[CH3:17]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 812191,3-Bis(diphenylphosphino)propaneHCID 69056351HCID 69056351, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 64764382HCID 64764382, compound

Reagents, catalysts & solvents 2

HCID 6436379Rhodium, di-mu-chlorobis((1,2,5,6-eta)-1,5-cyclooctadiene)di-CatalystHCID 887MethanolSolvent

Procedure

A solution of 0.41 g (1.38 mmol) of 1-[2-(4-bromo-2-vinylphenoxy)ethyl]pyrrolidine and 0.41 mL (2.94 mmol) of triethylamine in 25 mL of MeOH was degassed with argon and then combined with 35.5 mg (0.072 mmol) of bis(1,5-cyclooctadiene)dirhodium (I) dichloride and 57.1 mg (0.138 mmol) of 1,3-bis(diphenylphosphino)propane. The mixture was hydrogenated at RT and 3 bar hydrogen pressure. The reaction mixture was evaporated down in vacuo, and the residue was stirred with EtOAc, filtered, and the filtrate was evaporated down in vacuo. Yield: 0.26 g (87% of theoretical); C14H21NO (M=219.330); calc.: molpeak (M+H)+: 220; found: molpeak (M+H)+: 220.

Workup

  1. customwas hydrogenated at RT
  2. customThe reaction mixture was evaporated down in vacuo
  3. filtrationfiltered
  4. customthe filtrate was evaporated down in vacuo

Sources & evidence

ORD record
ord-60640f3e9478437e9c146041689b39d3
Source dataset
uspto-grants-2009_09
Patent number
US07592358B2

Reaction notes

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