4-Toluenesulfonyl chloride → Toluene-4-sulfonic acid 4-benzylamino-3-methyl-cyclohexylmethyl ester

HRID 1914661Notes

Reaction equation

HRID 1914661 reaction equation
[CH2:1]([NH:8][CH:9]1[CH2:14][CH2:13][CH:12]([CH2:15][OH:16])[CH2:11][CH:10]1[CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:18](Cl)([C:21]1[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=1)(=[O:20])=[O:19]>C(Cl)Cl.N1C=CC=CC=1>[CH2:1]([NH:8][CH:9]1[CH2:14][CH2:13][CH:12]([CH2:15][O:16][S:18]([C:21]2[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=2)(=[O:20])=[O:19])[CH2:11][CH:10]1[CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 67185026(4-Benzylamino-3-methyl-cyclohexyl)-methanol

Product 1

HCID 86638966Toluene-4-sulfonic acid 4-benzylamino-3-methyl-cyclohexylmethyl ester

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

(4-Benzylamino-3-methyl-cyclohexyl)-methanol (0.1 g, 3.00 mmol) in DCM (30 mL) and pyridine (3 mL) is treated with TsCl (0.86 g, 4.50 mmol) and the resulting mixture is stirred at RT overnight. The reaction mixture is partitioned between DCM and water and the organic portion is separated, dried (MgSO4) and concentrated in vacuo. Purification by chromatography on silica eluting with iso-hexane:EtOAc (1:2 increasing to 1:4) affords the title compound. 1H NMR (400 MHz, DMSO-d6) δ 7.78 (2H, d), 7.50 (2H, d), 7.30 (4H, m), 7.20 (1H, m), 3.80 (2H, d), 3.63 (2H, q), 2.41 (4H, m), 2.01 (1H, m), 1.72 (2H, m), 1.58 (1H, m), 1.49 (2H, m), 1.20 (1H, m), 1.02 (1H, m), 0.85 (1H, m), 0.81 (3H, d).

Workup

  1. customThe reaction mixture is partitioned between DCM and water
  2. customthe organic portion is separated
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customPurification by chromatography on silica eluting with iso-hexane:EtOAc (1:2 increasing to 1:4)

Sources & evidence

ORD record
ord-972f4ee957d04f57bc8ecd575d58dbcc
Source dataset
uspto-grants-2013_12
Patent number
US08614213B2

Reaction notes

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