Triethylamine → HCID 86670047, compound

HRID 69098Notes

Reaction equation

HRID 69098 reaction equation
[N:1]1([CH2:15][C:16]2[O:20][C:19]([CH2:21][OH:22])=[N:18][CH:17]=2)[CH2:6][CH2:5][C:4]2([C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH:8]=[CH:7]2)[CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:30][S:31](Cl)(=[O:33])=[O:32]>C(Cl)Cl>[CH3:30][S:31]([O:22][CH2:21][C:19]1[O:20][C:16]([CH2:15][N:1]2[CH2:6][CH2:5][C:4]3([C:14]4[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=4)[CH:8]=[CH:7]3)[CH2:3][CH2:2]2)=[CH:17][N:18]=1)(=[O:33])=[O:32]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68194670[5-(Spiro[indene-1,4'-piperidine]-1'-ylmethyl)oxazol-2-yl]methanol

Product 1

HCID 86670047HCID 86670047, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. stirred solution of [5-(spiro[indene-1,4′-piperidine]-1′-ylmethyl)oxazol-2-yl]methanol (0.15 g, 0.51 mmol) in DCM (10.0 mL) is added triethylamine (0.18 mL, 1.26 mmol) and methane sulphonyl chloride (0.05 mL, 0.61 mmol). The reaction mixture is stirred at 0° C. for 1 hour. The reaction mixture is washed with water (20.0 mL) and brine (10.0 mL), extracted with DCM, dried over Na2SO4, and evaporated to dryness to give the crude product (0.18 g) as a brown liquid.

Workup

  1. washThe reaction mixture is washed with water (20.0 mL) and brine (10.0 mL)
  2. extractionextracted with DCM
  3. dry with materialdried over Na2SO4
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-357187c547da4452a5c71128d8bf9c63
Source dataset
uspto-grants-2014_09
Patent number
US08822486B2

Reaction notes

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