Triethylamine → 2-[2-(Hydroxymethyl)pyrrolidin-1-yl]acetonitrile
Reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[CH2:6][OH:7].Br[CH2:9][C:10]#[N:11].CCN(CC)CC>C1COCC1>[OH:7][CH2:6][CH:2]1[CH2:3][CH2:4][CH2:5][N:1]1[CH2:9][C:10]#[N:11]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
The method follows that of S3 using 2-pyrrolidinemethanol (24.27 g, 0.241 mol), BrCH2CN (31.81 g, 0.265 mol), Et3N (37 mL, 0.265 mol) and dry THF (150 mL). The product was obtained as a straw-coloured oil (21.60 g, 64%) after purification by flash chromatography using ether/CH3OH (19:1). δH (250 MHz; CDCl3); 1.5-2.0 (m, 5H, CH2CH2CH2, CH2CH2CH, OH), 2.7 (m, 1H), 2.85 (m, 1H), 3.05 (m, 1H), 3.45 (2×d, 1H, J=4 Hz and J=11 Hz, 1×CHCH2OH), 3.65 (2×d, 1H, J=4 Hz and 11 Hz, 1×CHCH2OH) and 3.75 (d, 2H, NCH2CN); δC(62.9 MHz; CDCl3); 23.37, 27.45, 40.96, 53.95, 62.43, 63.06 and 115.48(CN); IR υmax/cm−1; 3375 (NH2), 3300 (NH2), 3200 (OH), 2970-2800 (CH2, CH3), 1600, 1475, 1375, 1230 and 1060; FAB MS, m/z(M+H)+ 141.
Sources & evidence
- ORD record
- ord-f55ecfdc5d664075ae181d5ede284397
- Source dataset
- uspto-grants-2009_07
- Patent number
- US07557215B2
Reaction notes
Loading…