Triethylamine → HCID 178486038, compound

HRID 25623Notes

Reaction equation

HRID 25623 reaction equation
[C:1]([O:5][C:6](=[O:20])[N:7]([C@H:9]1[CH2:14][CH2:13][C@H:12]([CH2:15][CH2:16][CH2:17][CH2:18][OH:19])[CH2:11][CH2:10]1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>C(Cl)Cl>[C:1]([O:5][C:6]([N:7]([CH3:8])[C@H:9]1[CH2:10][CH2:11][C@H:12]([CH2:15][CH2:16][CH2:17][CH2:18][O:19][S:29]([CH3:28])(=[O:31])=[O:30])[CH2:13][CH2:14]1)=[O:20])([CH3:3])([CH3:2])[CH3:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 178486036HCID 178486036, compound

Product 1

HCID 178486038HCID 178486038, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred, ice-cooled solution of 1.37 g (4.8 mmol) of trans-[4-(4-Hydroxy-butyl)-cyclohexyl]-methyl-carbamic acid tert-butyl ester and 0.95 ml NEt3 in 15 ml CH2Cl2 was added 0.5 ml (6.8 mmol) methanesulfonyl chloride. After stirring at RT for 2 h, the reaction mixture was partitioned between Et2O, 1M HCl and water. The ether-layer was concentrated in vacuo to give 1.745 g of clean trans-Methanesulfonic acid 4-[4-(tert-butoxycarbonyl-methyl-amino)-cyclohexyl]-butyl ester, that was treated in 5 ml CH2Cl2 with 5 ml of trifluoro acetic acid. After stirring the solution for 30 min at RT, the solution was evaporated under reduced pressure to dryness to give 2.25 g (quant.) trans-Methanesulfonic acid 4-(4-methylamino-cyclohexyl)-butyl ester.trifluoro-acetic acid.

Workup

  1. customthe reaction mixture was partitioned between Et2O, 1M HCl and water
  2. concentrationThe ether-layer was concentrated in vacuo

Sources & evidence

ORD record
ord-b0e1e52198b6440b8eba065c594e5bbd
Source dataset
uspto-grants-2005_02
Patent number
US06858651B2

Reaction notes

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