Diisopropylethylamine → HCID 178483630, compound

HRID 967174Notes

Reaction equation

HRID 967174 reaction equation
Cl.[CH3:2][NH:3][CH2:4][CH2:5][C@H:6]1[CH2:11][CH2:10][C@H:9](/[CH:12]=[CH:13]/[CH2:14][OH:15])[CH2:8][CH2:7]1.Cl[C:17]([O:19][C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=1)=[O:18].C(N(C(C)C)CC)(C)C>ClCCl.CCOCC>[Cl:26][C:23]1[CH:24]=[CH:25][C:20]([O:19][C:17](=[O:18])[N:3]([CH2:4][CH2:5][C@H:6]2[CH2:11][CH2:10][C@H:9](/[CH:12]=[CH:13]/[CH2:14][OH:15])[CH2:8][CH2:7]2)[CH3:2])=[CH:21][CH:22]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 1390594-Chlorophenyl chloroformateHCID 178483629HCID 178483629, compound

Product 1

HCID 178483630HCID 178483630, compoundYield 64.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 150 mg (0.642 mmol) trans-3-[4-(2-methylamino-ethyl)-cyclohexyl]-(E)-prop-2-en-1-ol HCl-salt and 125 mg (0.654 mmol) 4-chlorophenyl chloroformate in 1.5 ml of dichloromethane was added at room temperature 0.55 ml (3.21 mmol) diisopropyl ethyl amine. The reaction mixture was stirred for 1 hour at room temperature, taken up in ether and washed with 1N hydrogen chloride solution and water. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure and the residue then chromatographed on silica gel with a 2:1 v/v mixture of hexane and ethylacetate as the eluent giving 146 mg (64.7%) trans-{2-[4-(3-hydroxy-(E)-propenyl)-cyclohexyl]-ethyl}-methyl-carbamic acid 4-chloro-phenyl ester, MS: 369 (MNH4+, 1Cl).

Workup

  1. washwashed with 1N hydrogen chloride solution and water
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customthe residue then chromatographed on silica gel with a 2:1 v/v mixture of hexane and ethylacetate as the eluent

Sources & evidence

ORD record
ord-df11824605224a9bb3cf4d4812e265ff
Source dataset
uspto-grants-2005_10
Patent number
US06953806B2

Reaction notes

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