Bromide ion → HCID 58485261, compound

HRID 403593Notes

Reaction equation

HRID 403593 reaction equation
[C:1]([N:5]([CH2:10][CH2:11][C:12](=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:6](=[O:9])[O:7][CH3:8])([CH3:4])([CH3:3])[CH3:2].[Br-].[CH2:21]1[CH2:25]OC[CH2:22]1>>[C:1]([N:5]([CH2:10][CH2:11][C:12]([OH:19])([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:25][CH:21]=[CH2:22])[C:6](=[O:9])[O:7][CH3:8])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 259Bromide ionHCID 8028TetrahydrofuranHCID 58485273HCID 58485273, compound

Product 1

HCID 58485261HCID 58485261, compoundYield 46%

Procedure

To a solution of methyl tert-butyl(3-oxo-3-phenylpropyl)carbamate (2.0 g, 7.6 mmol) in THF (200 mL) was added allymagnesium bromide (1 M, 23 mL, 23 mmol) dropwise at −78° C. under N2. After adding completely, the reaction mixture was stirred at rt overnight. The reaction was quenched with saturated aqueous NH4Cl solution, and the mixture was extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated to give the crude product, which was purified by preparative TLC to afford methyl tert-butyl(3-hydroxy-3-phenylhex-5-enyl)carbamate (1.05 g, 46%). 1H NMR (CDCl3): 1.12-1.31 (s, 9H), 1.83-1.91 (m, 1H), 2.05-2.11 (m, 1H), 2.38-2.48 (m, 1H), 2.58-2.63 (m, 1H), 2.93-3.01 (m, 1H), 3.21-3.31 (m, 1H), 3.56 (s, 3H), 5.01-5.12 (m, 2H), 5.45-5.56 (m, 1H), 7.15-7.19 (m, 1H), 7.21-7.36 (m, 4H).

Workup

  1. additionAfter adding completely
  2. customThe reaction was quenched with saturated aqueous NH4Cl solution
  3. extractionthe mixture was extracted with EtOAc
  4. washThe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give the crude product, which
  9. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-c720585396484faf841c0546fc704eec
Source dataset
uspto-grants-2014_06
Patent number
US08748444B2

Reaction notes

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