HCID 10560838, compound → HCID 10584225, compound

HRID 1737295Notes

Reaction equation

HRID 1737295 reaction equation
[CH2:1]([C:8]1([NH:14][CH:15]=O)[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CCCCCC.CCOC(C)=O>[O:11]1[CH2:12][CH2:13][C:8]2([CH2:1][C:2]3[C:7](=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:15]=[N:14]2)[CH2:9][CH2:10]1

Participants

3

Reactant 1

HCID 10560838HCID 10560838, compound

Product 1

HCID 10584225HCID 10584225, compound

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Formamide 19 (1.00 g, 4.57 mmol) from the previous experiment is cyclized according to general procedure C to give the imine 21 as a yellow oil after FC (1:1 hexane/EtOAc, then EtOAc). The yield is 0.38 g (41%). 1H NMR (CDCl3) 8.35(s,1), 7.45-7.30(m,3), 7.16(d,1,J=7.0), 4.05-3.95(m,2), 3.80-3.70(m,2), 2.75(s,2), 1.80-1.60(m,4); 13C NMR (CDCl3) 158.21, 134.50, 131.33, 128.25, 128.05, 127.18, 127.13, 63.72, 53.85, 37.29, 37.13; MS(MW=201.3, EI, eE=70 eV) m/z 201(M+), 200, 186, 170, 156 (base peak), 144, 118, 115, 102, 89, 77, 63, 51, 41.

Sources & evidence

ORD record
ord-f9babb3b71d1448497ee5b0947702f78
Source dataset
uspto-grants-1999_10
Patent number
US05962469

Reaction notes

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