Sodium Carbonate → HCID 59596691, compound

HRID 2264826Notes

Reaction equation

HRID 2264826 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[N:12]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@H:11]([C:20]([O:22][CH3:23])=[O:21])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].CC1(C)C(C)(C)OB(/[CH:38]=[CH:39]/[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)O1.O1CCOCC1>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.O>[C:40]1(/[CH:39]=[CH:38]/[C:2]2[CH:7]=[CH:6][C:5]([C@@H:8]3[N:12]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@H:11]([C:20]([O:22][CH3:23])=[O:21])[CH2:10][CH2:9]3)=[CH:4][CH:3]=2)[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 57084134,4,5,5-tetramethyl-2-((E)-2-phenylethenyl)-1,3,2-dioxaborolaneHCID 59596707HCID 59596707, compound

Product 1

HCID 59596691HCID 59596691, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

In a vial containing 1-(1,1-dimethylethyl) 2-methyl (2S,5R)-5-(4-bromophenyl)-1,2-pyrrolidinedicarboxylate (D78, 100 mg, 0.26 mmol), sodium carbonate (138 mg, 1.30 mmol), 4,4,5,5-tetramethyl-2-[(E)-2-phenylethenyl]-1,3,2-dioxaborolane (90 mg, 0.39 mmol) and Pd(PPh3)4 (30 mg, 0.026 mmol) were added dioxane (2 ml) and water (1 ml). The mixture was stirred for 2 h at 80° C. After cooling, the mixture was extracted with ethyl acetate. The organic layer was filtered by phase separator tube and evaporated. The residue was purified by chromatography on silica gel using cyclohexane/ethyl acetate (1:0 to 9:1) to afford the title compound as a light yellow solid (90 mg, 85%). Rt (HPLC): 7.02 min; MS: (ES/+) m/z: 308 (MH-Boc) C25H29NO4 requires 407.

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. filtrationThe organic layer was filtered by phase separator tube
  4. customevaporated
  5. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-e12316f0da994de6a86e48fe8fe28f29
Source dataset
uspto-grants-2010_12
Patent number
US07855218B2

Reaction notes

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