Triethylamine → HCID 86697766, compound

HRID 2279829Notes

Reaction equation

HRID 2279829 reaction equation
[CH2:1]([O:8][CH2:9][C:10]1([CH2:14][OH:15])[CH2:13][O:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>C(Cl)Cl>[CH3:23][S:24]([O:15][CH2:14][C:10]1([CH2:9][O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:13][O:12][CH2:11]1)(=[O:26])=[O:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 20063122{3-[(Benzyloxy)methyl]oxetan-3-yl}methanol

Product 1

HCID 86697766HCID 86697766, compoundYield 523.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

An ice cooled solution of (3-(benzyloxymethyl)oxetan-3-yl)methanol (Example 44E, 1.00 g, 4.80 mmol) in DCM (5.14 mL) was treated with triethylamine (1.31 mL, 9.43 mmol) and methanesulfonyl chloride (0.438 mL, 5.66 mmol) and gradually allowed to warm up to rt over 16 hrs. The mixture was diluted with DCM, washed with saturated aqueous NaHCO3 solution (1×), brine (2×), dried over anhydrous sodium sulfate, filtered, concentrated in vacuo to a solid to afford 7.2 g of the title compound (100%). The crude product was used in next step without further purification. 1H NMR (400 MHz, CD3OD) δ 7.23-7.38 (m, 5H), 4.58 (s, 2H), 4.46-4.54 (m, 6H), 3.74 (s, 2H), 3.09 (s, 3H).

Workup

  1. washwashed with saturated aqueous NaHCO3 solution (1×), brine (2×)
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo to a solid

Sources & evidence

ORD record
ord-ec4f16da38ed4709bc8b95f3850f12df
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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