Water → HCID 59578062, compound

HRID 2194124Notes

Reaction equation

HRID 2194124 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH2:11][C:10]3([CH2:17][CH2:16][N:15]([S:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[O:27][C:28]([F:31])([F:30])[F:29])(=[O:20])=[O:19])[CH2:14][CH2:13]3)[C:9]2=[O:32])=[CH:4][CH:3]=1.O.C([O-])([O-])=O.[K+].[K+].B1(/[CH:49]=[CH:50]/[CH2:51][O:52][CH3:53])OC(C)(C)C(C)(C)O1>C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[CH3:53][O:52][CH2:51]/[CH:50]=[CH:49]/[C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:12][CH2:11][C:10]3([CH2:13][CH2:14][N:15]([S:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[O:27][C:28]([F:30])([F:29])[F:31])(=[O:19])=[O:20])[CH2:16][CH2:17]3)[C:9]2=[O:32])=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 162174432-[(1E)-3-methoxyprop-1-en-1-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 59577881HCID 59577881, compound2×

Product 1

HCID 59578062HCID 59578062, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

2-(4-Iodo-phenyl)-8-(2-trifluoromethoxy-benzenesulfonyl)-2,8-diaza-spiro[4.5]decan-1-one (0.01 g), product of example 104), was taken up in a mixture of ethanol (1 ml), water (1 ml) and toluene (8 ml), treated with K2CO3 (0.071 g) and (E)-2-(3-methoxypropenyl)-4,4,5,5-tetramethyl-(1,3,2)-dioxaboroane and stirred 30 minutes at RT under an argon atmosphere. Then tetrakis(triphenylphosphine)palladium(0) (0.02 g) was added and the mixture was heated at 85° C. for 4 h. It was then cooled to RT, partitioned between AcOEt and water, the layers were separated, the organic layer was dried over sodium sulphate, the solvent was removed in vacuo and the residue chromatographed over silica gel (AcOEt/heptane, gradient from 0 to 50%) to give the desired 2-[4-((E)-3-methoxy-propenyl)-phenyl]-8-(2-trifluoromethoxy-benzenesulfonyl)-2,8-diaza-spiro[4.5]decan-1-one (0.077 g) as an off white solid. MS (ESI): 525.16 (MH+).

Workup

  1. temperaturethe mixture was heated at 85° C. for 4 h
  2. temperatureIt was then cooled to RT
  3. custompartitioned between AcOEt and water
  4. customthe layers were separated
  5. dry with materialthe organic layer was dried over sodium sulphate
  6. customthe solvent was removed in vacuo
  7. customthe residue chromatographed over silica gel (AcOEt/heptane, gradient from 0 to 50%)

Sources & evidence

ORD record
ord-5b78d1139d7f4ab99d14f8591fbfb144
Source dataset
uspto-grants-2012_12
Patent number
US08329904B2

Reaction notes

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