Triethylamine → (Tetrahydrofuran-3-yl)methyl methanesulfonate

HRID 1011051Notes

Reaction equation

HRID 1011051 reaction equation
[O:1]1[CH2:5][CH2:4][C@@H:3]([CH2:6][OH:7])[CH2:2]1.ClC1N=C2C(N=CN2CC2CCOCC2)=C(Cl)N=1.C(N(CC)CC)C.[CH3:33][S:34](Cl)(=[O:36])=[O:35]>ClCCl>[CH3:33][S:34]([O:7][CH2:6][CH:3]1[CH2:4][CH2:5][O:1][CH2:2]1)(=[O:36])=[O:35]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 40784875((3S)-oxolan-3-yl)methanolHCID 576997032,6-Dichloro-9-(tetrahydro-2H-pyran-4-ylmethyl)-9H-purine

Product 1

HCID 22273010(Tetrahydrofuran-3-yl)methyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To (3S)-tetrahydro-3-furanylmethanol, Isomer 2 (1.4 g) in dry dichloromethane (40 ml) at 0° C. and under nitrogen, was added triethylamine (3.83 ml) followed by methanesulfonyl chloride (1.39 ml). The reaction was stirred at room temperature overnight. The orange solution was diluted with dichloromethane (50 ml) and washed with saturated aqueous sodium bicarbonate (20 ml). The organic layer was separated, dried through a hydrophobic frit and concentrated in vacuo to yield the title compound as an orange oil (2.6 g).

Workup

  1. washwashed with saturated aqueous sodium bicarbonate (20 ml)
  2. customThe organic layer was separated
  3. customdried through a hydrophobic frit
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0def901c17794d9ea04c6a765e5289bd
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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