HCID 69217817, compound → HCID 69217550, compound

HRID 2113404Notes

Reaction equation

HRID 2113404 reaction equation
[C:1]([C@@H:3]([NH2:23])[C@@H:4]([CH3:22])[C@@H:5]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)#[N:2]>C(Cl)(Cl)Cl>[C:1]([CH:3]([NH2:23])[C@@H:4]([CH3:22])[C@@H:5]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:6][CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)#[N:2]

Participants

3

Reactant 1

HCID 69217817HCID 69217817, compound

Product 1

HCID 69217550HCID 69217550, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

(1S,2R,3S)-1-cyano-2-methyl-3-benzyloxy-N-benzylbutylamine (1S)-(15) [α]D=−12° (c 3.6; CHCl3); IR (CHCl3) 3343, 3090, 3068, 3031, 3013, 2979, 2935, 2880, 2226, 1605, 1587, 1497, 1455, 1386, 1378, 1359, 1333, 1232 cm−1; 1H NMR (250 MHz, CDCl3) δ 7.34 to 7.22 (m, 10H); 4.59 (d, J=11.2 Hz, 1H); 4.37 (d, J=11.2 Hz, 1H); 4.04 (d, J=12.8 Hz, 1H); 3.97 (d, J=4.7 Hz, 1H); 3.79 (d, J=12.8 Hz, 1H); 3.50 (dq, J=8.8; 6.1 Hz, 1H); 2.07 to 1.93 (m, 1H); 1.62 (broad s, 1H, NH); 1.22 (d, J=6.0 Hz, 3H); 1.04 (d, J=6.9 Hz, 3H); 13C NMR (62.5 MHz, CDCl3) δ 138.3; 138.0; 128.4; 128.3; 127.6; 127.5; 127.4; 119.1; 76.0; 70.8; 51.9; 51.5; 42.4; 16.4; 11.7; MS (CI) m/z 309 [M+H]+. HRMS: calculated for C20H25N2O (M+H), 309.19668; found, 309.19321.

Sources & evidence

ORD record
ord-90ffb3dc2b284ec3b8248a531fb19fed
Source dataset
uspto-grants-2008_10
Patent number
US07432087B2

Reaction notes

Loading…