Triethylamine → (4-Fluorotetrahydro-2h-pyran-4-yl)methyl methanesulfonate

HRID 574826Notes

Reaction equation

HRID 574826 reaction equation
[F:1][C:2]1([CH2:8][OH:9])[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.[CH3:10][S:11](Cl)(=[O:13])=[O:12].C(N(CC)CC)C>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:10][S:11]([O:9][CH2:8][C:2]1([F:1])[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1)(=[O:13])=[O:12]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 56971676(4-Fluorooxan-4-yl)methanol

Product 1

HCID 87279396(4-Fluorotetrahydro-2h-pyran-4-yl)methyl methanesulfonate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of EXAMPLE 37C (1.4 g), methanesulfonyl chloride (1.054 mL), triethylamine (2.99 mL), and 4-dimethylaminopyridine (0.051 g) in CH2Cl2 (20 mL) was stirred at 0° C. for 2 hours, concentrated and chromatographed on silica gel eluting with 30% ethyl acetate in hexanes to give the product.

Workup

  1. concentrationconcentrated
  2. customchromatographed on silica gel eluting with 30% ethyl acetate in hexanes
  3. customto give the product

Sources & evidence

ORD record
ord-63d06f0960464a13bafd793f9089f6a6
Source dataset
uspto-grants-2015_05
Patent number
US09034875B2

Reaction notes

Loading…