Water → HCID 68559484, compound

HRID 2036081Notes

Reaction equation

HRID 2036081 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][OH:9].C([Li])CCC.[O:15]=[C:16]1[CH2:19][N:18]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:17]1.O>O1CCCC1>[OH:15][C:16]1([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[CH2:8][OH:9])[CH2:17][N:18]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:19]1

Participants

6

Reactant 4

HCID 962WaterHCID 728502-Bromobenzyl alcoholHCID 15194043-Oxo-azetidine-1-carboxylic acid tert-butyl esterHCID 178418339Butyllithium

Product 1

HCID 68559484HCID 68559484, compoundYield 61.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (2-bromophenyl)methanol (4.4 g) in dry tetrahydrofuran (90 mL) was added n-butyllithium (1.6 M hexane solution, 31 mL) at −78° C., and the mixture was warmed to room temperature over 2 hr. A solution of tert-butyl 3-oxoazetidine-1-carboxylate (4.0 g) in dry tetrahydrofuran (30 mL) was added at −78° C., and the mixture was stirred at room temperature for 18 hr. The reaction solution was poured into water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over sodium sulfate and concentrated. The residue was purified by silica gel column chromatography (50% ethyl acetate/hexane to 60% ethyl acetate/hexane) to give the object product (4.0 g, 61%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (50% ethyl acetate/hexane to 60% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-5a027b08898344ea9b802fc6bf4d26d8
Source dataset
uspto-grants-2013_11
Patent number
US08575167B2

Reaction notes

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