Triethylamine → HCID 86743064, compound

HRID 2165169Notes

Reaction equation

HRID 2165169 reaction equation
[CH2:1]([O:3][C:4]([C@H:6]1[C@H:11]([OH:12])[CH2:10][CH2:9][N:8]([CH2:13][C:14]2[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[CH:15]=2)[CH2:7]1)=[O:5])[CH3:2].C(N(CC)CC)C.[CH3:29][S:30]([Cl:33])(=[O:32])=[O:31]>CN(C)C1C=CN=CC=1.ClCCl>[ClH:33].[CH2:1]([O:3][C:4]([C@H:6]1[C@H:11]([O:12][S:30]([CH3:29])(=[O:32])=[O:31])[CH2:10][CH2:9][N:8]([CH2:13][C:14]2[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[CH:15]=2)[CH2:7]1)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 70358194HCID 70358194, compound

Product 1

HCID 86743064HCID 86743064, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

3.8 g (13 mmol) of trans-4-hydroxy-1-[(benzocyclobuten-1-yl)methyl]-piperidine-3-carboxylic acid ethyl ester, 3.6 ml (26 mmol) of triethylamine and 1.8 g (14 mmol) of 4-dimethylaminopyridine are introduced into 100 ml of dichloromethane. 1.1 ml of methanesulphonic acid chloride are added thereto at room temperature. Stirring is then carried out for 30 hours, and the reaction mixture is diluted with dichloromethane, washed 3 times with water and dried over sodium sulphate. The crude product is purified by chromatography on silica gel. The purified product is converted into the hydrochloride with ethanolic hydrochloric acid and crystallised by adding diethyl ether. Trans-1-[(benzocyclobuten-1-yl)methyl]-4-methanesulphonyloxypiperidine-3-carboxylic acid ethyl ester hydrochloride of m.p. 145°-146° C. is obtained.

Workup

  1. customat room temperature
  2. washwashed 3 times with water
  3. dry with materialdried over sodium sulphate
  4. customThe crude product is purified by chromatography on silica gel
  5. customcrystallised
  6. additionby adding diethyl ether

Sources & evidence

ORD record
ord-78beec7c03a04fc992e0580f77e1342d
Source dataset
uspto-grants-1990_07
Patent number
US04939160

Reaction notes

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