Water → HCID 86618699, compound

HRID 2239378Notes

Reaction equation

HRID 2239378 reaction equation
[OH:1][CH2:2][C:3]1[N:8]=[C:7]([O:9][CH2:10][C@H:11]2[CH2:15][CH2:14][CH2:13][N:12]2[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:6]=[CH:5][CH:4]=1.[CH3:23][S:24](Cl)(=[O:26])=[O:25].CCN(C(C)C)C(C)C.O>C(Cl)Cl>[CH3:23][S:24]([O:1][CH2:2][C:3]1[N:8]=[C:7]([O:9][CH2:10][C@H:11]2[CH2:15][CH2:14][CH2:13][N:12]2[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:6]=[CH:5][CH:4]=1)(=[O:26])=[O:25]

Participants

6

Reactant 4

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 86618698HCID 86618698, compound

Product 1

HCID 86618699HCID 86618699, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

tert-Butyl (2R)-2-({[6-(hydroxymethyl)pyridin-2-yl]oxy}methyl)pyrrolidine-1-carboxylate (430 mg, 1.4 mmol) was dissolved in DCM (15 mL) and MsCl (240 mg, 2.1 mmol) was added. The reaction mixture was cooled to 0° C. and DIPEA (0.72 mL, 4.1 mmol) were added. The reaction mixture was stirred 2 h at ambient temperature and water was added. The organic phase was separated and evaporated. The residue was purified by flash chromatography using a gradient of EtOAc/heptane to give the title compound as a clear oil. Yield: 420 mg (78%). 1H NMR (399.961 MHz, CDCl3) δ 7.61 (t, J=8.2 Hz, 1H), 7.01 (d, J=6.6 Hz, 1H), 6.72 (d, J=8.5 Hz, 1H), 5.20 (s, 2H), 4.49-4.30 (m, 1H), 4.27-4.06 (m, 2H), 3.50-3.27 (m, 2H), 3.07 (s, 3H), 2.04-1.90 (m, 3H), 1.90-1.81 (m, 1H), 1.46 (s, 9H). MS (ESI+) 387.2 (M+1H+).

Workup

  1. customThe organic phase was separated
  2. customevaporated
  3. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-928bfc9a076947778fadafb1654d6cd0
Source dataset
uspto-grants-2010_05
Patent number
US07723331B2

Reaction notes

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