Benzylamine → (+)-1-(1-Phenyl-2-propenyl)pyrrolidine

HRID 14437Notes

Reaction equation

HRID 14437 reaction equation
[CH2:1]([NH2:8])[C:2]1C=CC=[CH:4][CH:3]=1.C(=O)(O[CH2:13][CH:14]=[CH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)OC.N1CCCC1>C1COCC1>[C:16]1([CH:15]([N:8]2[CH2:1][CH2:2][CH2:3][CH2:4]2)[CH:14]=[CH2:13])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 31268PyrrolidineHCID 54135828Methyl 3-phenylprop-2-en-1-yl carbonate2×

Product 1

HCID 10081167(+)-1-(1-Phenyl-2-propenyl)pyrrolidineYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stock solution containing [(COD)IrCl]2 (3.4 mg, 0.0050 mmol) and L1 (10.8 mg, 0.0200 mmol) in 1.0 mL of THF was prepared. By the procedure for reaction of benzylamine with methyl cinnamyl carbonate, the reaction of pyrrolidine (85.0 mg, 1.19 mmol) and methyl cinnamyl carbonate (201.5 mg, 1.049 mmol) was conducted at room temperature for 16 h. 1H NMR analysis of the crude mixture showed the ratio of branched to linear product to be 99/1. After purification, 121 mg of the title compound (61%) was isolated and HPLC analysis as described above indicated that the enantiomeric excess of the major product was 97%.

Workup

  1. customwas prepared
  2. customAfter purification

Sources & evidence

ORD record
ord-ba32caefae8f4ace802b27d9f8200b10
Source dataset
uspto-grants-2010_06
Patent number
US07732365B2

Reaction notes

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