Triethylamine → (S)-1-Benzyl-3-mesyloxypyrrolidine

HRID 1666970Notes

Reaction equation

[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH2:6]([N:13]1[CH2:17][CH2:16][C@H:15]([OH:18])[CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH3:1][S:2]([O:18][C@H:15]1[CH2:16][CH2:17][N:13]([CH2:6][C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:14]1)(=[O:4])=[O:3]

Participants

Conditions

Temperature: 0 °C

Procedure

Methanesulfonyl chloride (15 mL, 0.19 mol) is added to a cooled (0° C.) solution of toluene (300 mL) containing (S)-1-benzylpyrrolidin-3-ol (24.5 g, 0.14 mol) and triethylamine (80 mL, 0.57 mol). The resulting mixture is stirred at 0° C. for 15 min, and allowed to warm to room temperature with stirring for 2 h. The mixture is quenched with a 5% aqueous solution of sodium bicarbonate (250 mL). The organic layer is washed with a 5% aqueous solution of sodium bicarbonate (2×250 mL), washed with water (1×250 mL), dried over magnesium sulfate, and concentrated under reduced pressure to give N (35.1 g, 99%) as an orange oil. 1H NMR (300 MHz, CDCl3): δ 2.07 (m, 1H), 2.30 (m, 1H), 2.49 (m, 1H), 2.75-2.90 (m, 3H), 2.98 (s, 3H), 3.61 (d, J=13.0 Hz, 1H), 3.68 (d, J=13.0 Hz, 1H), 5.18 (m, 1H), 7.15-7.30 (m, 5H). LCMS m/z calcd for C12H17NO3S 255 ([M+]). found 256 ([M+H]+, 100%), 160 (40%).

Workup

temperatureto warm to room temperature
stirringwith stirring for 2 h
customThe mixture is quenched with a 5% aqueous solution of sodium bicarbonate (250 mL)
washThe organic layer is washed with a 5% aqueous solution of sodium bicarbonate (2×250 mL)
washwashed with water (1×250 mL)
dry with materialdried over magnesium sulfate
concentrationconcentrated under reduced pressure
customto give N (35.1 g, 99%) as an orange oil

Sources & evidence

ORD record: ord-29dcde68144d4d8f8b4e68990e2309d0
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08044204B2

Reaction notes

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