Allyl bromide → (1R)-benzyl 3-allyl-3-hydroxycyclopentanecarboxylate
Reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][C@@H:4]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:3]1.[Cl-].[NH4+].Br[CH2:20][CH:21]=[CH2:22]>C1COCC1.[Zn]>[CH2:22]([C:2]1([OH:1])[CH2:6][CH2:5][C@@H:4]([C:7]([O:9][CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:8])[CH2:3]1)[CH:21]=[CH2:20]Participants
Conditions
- Temperature
- 80 °C
Procedure
To a solution of (R)-benzyl 3-oxocyclopentanecarboxylate (1 g, 4.58 mmol) in THF (10 mL) was added zinc powder (2.098 mL, 229 mmol), saturated aqueous ammonium chloride solution (20 mL) followed by 3-bromoprop-1-ene (1.663 g, 13.75 mmol) slowly at room temperature. The resulting mixture was heated to 80° C. for 3 hours, then allowed to stir at room temperature for additional 12 hours. The reaction mixture was filtered and the filtrate concentrated. To the residue was added ethyl acetate (20 mL) and the resulting mixture was washed with water (5 ml), brine (5 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure to yield (1R)-benzyl 3-allyl-3-hydroxycyclopentanecarboxylate (580 mg, 2.228 mmol, 48.6% yield) as an oil. It was used as such for the next step without further purification. MS (ESI+) m/z 283 (M+Na)+
Workup
- filtrationThe reaction mixture was filtered
- concentrationthe filtrate concentrated
- additionTo the residue was added ethyl acetate (20 mL)
- washthe resulting mixture was washed with water (5 ml), brine (5 mL)
- dry with materialdried over anhydrous Na2SO4
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-e1e97ce7d2d34f45965b4e1cc1ddc9e7
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08877749B2
Reaction notes
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