Benzyl Bromide → HCID 90079853, compound

HRID 1771962Notes

Reaction equation

HRID 1771962 reaction equation
[CH2:1]([C@H:4]([CH:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:9][CH:10]=[CH2:11])[C:5]([OH:7])=[O:6])[CH:2]=[CH2:3].C(=O)([O-])[O-].[K+].[K+].Br[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.CCOC(C)=O.CCCCCC>CN(C=O)C>[CH2:1]([C@H:4]([C@H:8]([CH2:9][CH:10]=[CH2:11])[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:5]([O:7][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:6])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 21226206Ethyl acetate hexaneHCID 90079841HCID 90079841, compound

Product 1

HCID 90079853HCID 90079853, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (2R)-2-allyl-3-(tert-butoxycarbonyl)hex-5-enoic acid, Intermediate S8E (1.8 g, 7.08 mmol) (anti:syn 4:1) in DMF (20 mL) at room temperature was added potassium carbonate (1.956 g, 14.16 mmol), followed by (bromomethyl)benzene (1.010 mL, 8.49 mmol). The reaction mixture was stirred at room temperature for 3 h and filtered to remove solid material. The filtrate was diluted with EtOAc and water. The organic layer was separated and washed with water, brine, dried over MgSO4, filtered, and concentrated to give a crude material. This crude material was purified with ISCO 80 g column, 60 mL/min. 0-20% EtOAc/hexane in 25 min to afford (2R,3S)-1-benzyl 4-tert-butyl 2,3-diallylsuccinate, Intermediate S8F (1.5 g, 4.35 mmol, 61.5% yield) as a colorless liquid. 1H NMR (400 MHz, chloroform-d) δ 7.43-7.31 (m, 5H), 5.81-5.62 (m, 2H), 5.17-5.08 (m, 2H), 5.08-4.96 (m, 4H), 2.84-2.63 (m, 2H), 2.45-2.23 (m, 3H), 2.18 (d, J=1.5 Hz, 1H), 1.43 (s, 9H).

Workup

  1. filtrationfiltered
  2. customto remove solid material
  3. additionThe filtrate was diluted with EtOAc and water
  4. customThe organic layer was separated
  5. washwashed with water, brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a crude material
  10. customThis crude material was purified with ISCO 80 g column, 60 mL/min

Sources & evidence

ORD record
ord-cbb134636a0d435faaaf25fddf96d055
Source dataset
uspto-grants-2016_02
Patent number
US09249157B2

Reaction notes

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