Triethylamine → 1-Methylpyrrolidin-3-yl methanesulfonate
Reaction equation
[OH:1][CH:2]1[CH2:6][CH2:5][N:4]([CH3:7])[CH2:3]1.CCN(CC)CC.[CH3:15][S:16](Cl)(=[O:18])=[O:17]>C(Cl)Cl.CN(C1C=CN=CC=1)C.C(Cl)(Cl)Cl>[CH3:15][S:16]([O:1][CH:2]1[CH2:6][CH2:5][N:4]([CH3:7])[CH2:3]1)(=[O:18])=[O:17]Participants
7
Conditions
- Temperature
- 0 °C
Procedure
3-Hydroxy-1-methylpyrroldine (0.543 mL, 4.94 mmol) was dissolved in DCM (10 mL) and cooled to 0° C. Et3N (0.827 mL, 5.93 mmol), methanesulfonyl chloride (0.421 mL, 5.44 mmol) and DMAP (0.006 g, 0.05 mmol) were added and the mixture was stirred for 16 hours at room temperature. The mixture was diluted with CHCl3 (5 mL) and washed with sat. NaHCO3 (5 mL) and water (2×5 mL). The organic layer was concentrated in vacuo to give the title compound A22 as a yellow oil (0.717 g, 81% yield). 1H NMR (300 MHz, CDCl3) δ 1.85-2.24 (m, 6H), 2.38-2.74 (m, 3H), 2.76-2.91 (m, 3H), 4.95 (m, 1H).
Workup
- washwashed with sat. NaHCO3 (5 mL) and water (2×5 mL)
- concentrationThe organic layer was concentrated in vacuo
Sources & evidence
- ORD record
- ord-e4deca4ab5fb43d48dfd380b94063ea5
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09238644B2
Reaction notes
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