HCID 178454090, compound → HCID 178454089, compound

HRID 2359637Notes

Reaction equation

HRID 2359637 reaction equation
[C:1]([O:5][C:6](=[O:14])[NH:7][C@H:8]1[CH2:11][C@H:10]([CH2:12][OH:13])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2]>ClCCl>[C:1]([O:5][C:6](=[O:14])[NH:7][C@H:8]1[CH2:11][C@H:10]([CH:12]=[O:13])[CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 178454090HCID 178454090, compound2×

Product 1

HCID 178454089HCID 178454089, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of trans-(3-hydroxymethyl-cyclobutyl)-carbamic acid tert-butyl ester (Compound 4a) (0.2 g; 1.0 mmol) in anhydrous dichloromethane (8.0 mL) at 0° C. was added 1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benzodioxol-3-(1H)-one (0.84 g; 2.0 mmol). The reaction was allowed to stir at room temperature under nitrogen for 3 h, before partitioning the reaction mixture between dichloromethane and brine. The organic layer was washed with brine, dried over Na2SO4, filtered, and the solvent evaporated in vacuo to yield a crude oil. The crude oil was purified via flash column chromatography, eluting with 30% ethyl acetate in hexanes, to yield Compound 4b as a foam (0.2 g; 88% yield). 1H NMR (400 MHz, CDCl3): δ 9.82 (1H, d), 4.77 (1H, br s), 4.16-4.11 (1H, br s), 3.04-3.03 (1H, m), 2.69-2.64 (2H, m), 2.21-2.13 (2H, m), 1.44 (9H, s).

Workup

  1. custombefore partitioning the reaction mixture between dichloromethane and brine
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent evaporated in vacuo
  6. customto yield a crude oil
  7. customThe crude oil was purified via flash column chromatography
  8. washeluting with 30% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-020b3611d09048d989216fad371e2466
Source dataset
uspto-grants-2014_04
Patent number
US08685990B2

Reaction notes

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