Pyridine → HCID 178418975, compound

HRID 2225212Notes

Reaction equation

HRID 2225212 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([OH:14])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>C(Cl)Cl>[C:1]([O:5][C:6]([NH:7][C@H:8]1[CH2:9][CH2:10][C@H:11]([O:14][S:23]([CH3:22])(=[O:25])=[O:24])[CH2:12][CH2:13]1)=[O:15])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 178418329HCID 178418329, compound

Product 1

HCID 178418975HCID 178418975, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (trans-4-hydroxy-cyclohexyl)-carbamic acid tert-butyl ester (7.0 g, 33 mmol) in CH2Cl2 (165 mL) was charged with pyridine (13 mL, 79 mmol) and methanesulfonylchloride (6.4 mL, 82 mmol). The reaction was stirred at RT for 14 h and concentrated in vacuo. The residue was dissolved in EtOAc and the resulting solution was washed successively with water (2×) and brine (1×) before being dried (MgSO4), filtered, and concentrated in vacuo to afford methanesulfonic acid trans-4-tert-butoxycarbonylamino-cyclohexyl ester (9.3 g, 96% yield). MS found: (M+H)+=294.2.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in EtOAc
  3. washthe resulting solution was washed successively with water (2×) and brine (1×)
  4. dry with materialbefore being dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4a9f60a1420f403f92e65fdba1567744
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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