Triethylamine → HCID 67378212, compound

HRID 1182733Notes

Reaction equation

HRID 1182733 reaction equation
[CH2:1]([N:8]1[CH2:14][CH2:13][CH2:12][C:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH2:22]O)([OH:15])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.CS(Cl)(=O)=O>O1CCCC1>[CH2:1]([N:8]1[CH2:14][CH2:13][CH2:12][C:11]2([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[CH2:22][O:15]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 31297Methanesulfonyl chlorideHCID 12532948HCID 12532948, compound

Product 1

HCID 67378212HCID 67378212, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (RS)-1-benzyl-4-(2-hydroxymethyl-phenyl)-azepan-4-ol (7.0 g, 22 mmol) and triethylamine (3.1 ml, 22 mmol) in tetrahydrofuran (80 ml) was added a solution of methanesulfonyl chloride (1.7 ml, 22 mmol) in tetrahydrofuran (20 ml) at 0° C. After completed addition the temperature was allowed to rise to room temperature. Stirring for 2 h was followed by addition of another portion of triethylamine (3.1 ml, 22 mmol). Stirring was continued over night. The reaction mixture was partitioned between water and ethyl acetate. The layers were separated and the organic layer was concentrated in vacuo. Flash column chromatography using heptane/ethyl acetate as eluent gave the title compound as a light yellow oil (4.0 g, 61%).

Workup

  1. additionaddition the temperature
  2. customto rise to room temperature
  3. stirringStirring
  4. waitwas continued over night
  5. customThe reaction mixture was partitioned between water and ethyl acetate
  6. customThe layers were separated
  7. concentrationthe organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-be1f6829356e4c849d6cd0103a557309
Source dataset
uspto-grants-2014_03
Patent number
US08664216B2

Reaction notes

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