N-Methyl dicyclohexylamine → HCID 66817656, compound

HRID 1755106Notes

Reaction equation

HRID 1755106 reaction equation
C1(N(C2CCCCC2)C)CCCCC1.[CH:15]([S:17]([N:20]1[CH2:29][CH2:28][C:23]2([O:27][CH2:26][CH2:25][O:24]2)[CH2:22][CH2:21]1)(=[O:19])=[O:18])=[CH2:16].Br[C:31]1[CH:39]=[CH:38][C:34]([C:35]([OH:37])=[O:36])=[CH:33][C:32]=1[CH3:40].F[B-](F)(F)F.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C>CN1C(=O)CCC1.C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[O:27]1[C:23]2([CH2:22][CH2:21][N:20]([S:17](/[CH:15]=[CH:16]/[C:31]3[CH:39]=[CH:38][C:34]([C:35]([OH:37])=[O:36])=[CH:33][C:32]=3[CH3:40])(=[O:18])=[O:19])[CH2:29][CH2:28]2)[O:24][CH2:25][CH2:26]1

Participants

8

Reactant 4

HCID 24210N-Methyl dicyclohexylamineHCID 821314-Bromo-3-methylbenzoic acidHCID 2734635Tri-tert-butylphosphine tetrafluoroborateHCID 66818416HCID 66818416, compound

Product 1

HCID 66817656HCID 66817656, compoundYield 94.1%

Reagents, catalysts & solvents 3

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
100 °C

Procedure

Dicyclohexyl-methyl-amine (34.2 ml, 162.8 mmol) was added to a solution of 8-ethenesulfonyl-1,4-dioxa-8-aza-spiro[4.5]decane (17.3 g, 74.01 mmol), 4-bromo-3-methyl-benzoic acid (19.1 g, 88.82 mmol), Pd(dba)2 (4.26 g, 7.40 mmol) and tri-t-butylphosphonium tetrafluoroborate (2.15 g, 7.40 mmol) in NMP (70.0 ml), and the mixture was stirred at 100° C. for one hour in a nitrogen atmosphere. The reaction solution was cooled to room temperature and then diluted with ethyl acetate, and the organic layer was washed with a 1 M aqueous hydrochloric acid solution and saline. The organic layer was allowed to stand for a while, and the precipitated solid was filtered off. The resulting solid was washed with ethyl acetate to give 4-[(E)-2-(1,4-dioxa-8-aza-spiro[4.5]decane-8-sulfonyl)-vinyl]-3-methyl-benzoic acid as a gray solid (25.6 g, 94.1%).

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. washthe organic layer was washed with a 1 M aqueous hydrochloric acid solution and saline
  3. filtrationthe precipitated solid was filtered off
  4. washThe resulting solid was washed with ethyl acetate

Sources & evidence

ORD record
ord-aaeb55a35cb043eba2fa0a07d49244d8
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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