Methyl iodide → HCID 67311021, compound

HRID 2061091Notes

Reaction equation

[CH3:1][C:2]([NH:11][C:12](=[O:21])[O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([CH2:4][CH2:5][N:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1)[CH3:3].[CH3:22][I:23]>C(O)C>[I-:23].[CH2:14]([O:13][C:12]([NH:11][C:2]([CH3:1])([CH3:3])[CH2:4][CH2:5][N+:6]1([CH3:22])[CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:21])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Benzyl 2-methyl-4-(pyrrolidin-1-yl)butan-2-ylcarbamate (4.81 g, 16.6 mmol) was placed into a 48 mL pressure vessel. Methyl iodide (10 mL, 10 equiv, 0.16 mol) was added to the reaction in one portion. No heat was evolved during addition, absolute ethanol (5 mL) was added to the vessel then it was sealed. The reaction was left to stir at 50° C. for 16 h. The blood red solution was concentrated to a dark red oil. The crude product was dissolved into a small amount of water and filtered through a 0.45 micron PTFE frit, then this solution was purified on a Shimadzu Prep-LC utilizing water/acetonitrile and 0.05% acetic acid as modifier. Fractions were collected monitoring UV absorbance at 215 nm. The fractions were pooled and lyophilized to give a colorless oil (5.24 g, 73.2%). 1H NMR (CDCl3, 400 MHz): δ 1.29 (s, 6H), 2.02-2.25 (m, 6H), 2.88 (s, 3H), 3.15-3.30 (m, 4H), 3.32-3.45 (m, 2H), 5.08 (s, 2H), 7.38-7.50 (m, 5H). LRMS (ESI+) for C18H29N2O2+ (305.2); Found: 305 (M+).

Workup

additionwas added to the vessel
customit was sealed
waitThe reaction was left
concentrationThe blood red solution was concentrated to a dark red oil
dissolutionThe crude product was dissolved into a small amount of water
filtrationfiltered through a 0.45 micron PTFE frit
customthis solution was purified on a Shimadzu Prep-LC
customFractions were collected

Sources & evidence

ORD record: ord-3e2612122a3c44f496366629b7d3b9a2
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08278482B2

Reaction notes

Loading…