4-Nitrobenzoic Acid → ((R)-2-Hydroxy-pent-4-enyl)-carbamic Acid benzyl ester

HRID 1096292Notes

Reaction equation

HRID 1096292 reaction equation
[CH2:1]([CH:4]1[CH2:6][O:5]1)[CH:2]=[CH2:3].[C:7](=[O:17])([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[NH2:8].[N+](C1C=CC(C(O)=O)=CC=1)([O-])=O>CC(OC)(C)C>[CH2:10]([O:9][C:7](=[O:17])[NH:8][CH2:6][C@H:4]([OH:5])[CH2:1][CH:2]=[CH2:3])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 61084-Nitrobenzoic AcidHCID 12136Benzyl carbamateHCID 126597812-Allyl-oxirane

Product 1

HCID 66783125((R)-2-Hydroxy-pent-4-enyl)-carbamic Acid benzyl esterYield 59.5%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

To a solution of 2-allyl-oxirane (Synthesis 1986, 309; 918 mg, 10.9 mmol) in TBME (12 mL) were added benzyl carbamate (750 mg, 4.96 mmol), 4-nitrobenzoic acid (146 mg, 0.87 mmol) and (1S,2S)-(+)-N—N′-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminocobalt(II) 264 mg, 0.44 mmol) at RT, then after 72 h the reaction mixture was partitioned between TBME and sat. aq. NaHCO3 solution. The organic layer was washed with brine, dried (MgSO4), filtered, and evaporated. Chromatography (SiO2; heptane-EtOAc gradient) produced the title compound (694 mg, 48%). Brown oil, MS: 236.2 (M+H)+.

Workup

  1. customafter 72 h the reaction mixture was partitioned between TBME and sat. aq. NaHCO3 solution
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-c9c7a7414ddb4f5ba05808c8dae19d4e
Source dataset
uspto-grants-2012_03
Patent number
US08138175B2

Reaction notes

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