Butyl ether → (+/-)-[[1-(2,5-Dihydro-1H-pyrrol-1-yl)cyclopentyl](phenyl)methyl]amine

HRID 20817Notes

Reaction equation

HRID 20817 reaction equation
[N:1]1([C:6]2([C:11]#[N:12])[CH2:10][CH2:9][CH2:8][CH2:7]2)[CH2:5][CH:4]=[CH:3][CH2:2]1.[C:13]1([Li])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(OCCCC)CCC.[BH4-].[Na+].NC(C1C=CC=CC=1)C1(N(C)C)CCCC1>C1COCC1.CO>[N:1]1([C:6]2([CH:11]([NH2:12])[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:10][CH2:9][CH2:8][CH2:7]2)[CH2:5][CH:4]=[CH:3][CH2:2]1

Participants

8

Reactant 5

HCID 8909Butyl etherHCID 4311764Sodium borohydrideHCID 11521393{1-[Amino(phenyl)methyl]cyclopentyl}dimethylamineHCID 593478621-(2,5-Dihydro-1H-pyrrol-1-yl)cyclopentanecarbonitrileHCID 178506676HCID 178506676, compound

Product 1

HCID 59347866(+/-)-[[1-(2,5-Dihydro-1H-pyrrol-1-yl)cyclopentyl](phenyl)methyl]amineYield 45%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The title compound (1.35 g; 45%) was prepared from 1-(2,5-dihydro-1H-pyrrol-1-yl)cyclopentanecarbonitrile D37 (2.0 g; 12.3 mmol), and phenyllithium in di-n-butylether (7.5 ml of 1.8M solution; 13.5 mmol) in THF (20 ml), followed by reaction with sodium borohydride (1.402 g; 36.9 mmol) in methanol (20 ml) in a similar manner to that described in D2. Mass Spectrum (Electrospray LC/MS): Found 243 (MH+). C16H22N2 requires 242. Ret. time 1.02 min.

Sources & evidence

ORD record
ord-774247e904624079aabbb34d35215d5f
Source dataset
uspto-grants-2010_06
Patent number
US07745642B2

Reaction notes

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