Triethylamine → HCID 86743064, compound

HRID 1762591Notes

Reaction equation

HRID 1762591 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-methanesulphonyloxy-piperidine-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-9dbd19014d834658a10f32640773f3e6
Source dataset
uspto-grants-1989_05
Patent number
US04833169

Reaction notes

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