Borane → HCID 178502739, compound

HRID 271350Notes

Reaction equation

HRID 271350 reaction equation
[CH3:1][O:2][N:3]([CH3:14])[C:4]([C@@H:6]1[CH2:9][C@H:8]([CH2:10][C:11](O)=[O:12])[CH2:7]1)=[O:5].B>C1COCC1>[CH3:1][O:2][N:3]([CH3:14])[C:4]([C@H:6]1[CH2:9][C@@H:8]([CH2:10][CH2:11][OH:12])[CH2:7]1)=[O:5]

Participants

4

Reactant 2

HCID 6331BoraneHCID 178502740HCID 178502740, compound

Product 1

HCID 178502739HCID 178502739, compoundYield 64.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To an ice cold solution of 3.0 g of cis-[3-(methoxy-methyl-carbamoyl)-cyclobutyl]-acetic acid in 50 mL of THF was added 15 mL of 1M borane in THF. The mixture was allowed to stir for 15 min in the cold, then warm and stir for 30 min. The reaction was quenched with 25 mL of 10% HCl and extracted into 3×50 mL of ethyl acetate. The combined extracts were diluted with 50 mL of toluene, dried over magnesium sulfate and concentrated under reduced pressure. Drying under vacuum overnight gave 1.8 g of product as a colorless oil: MS (m+1)=188.45; 1H NMR (400 MHz, CDCl3) 3.62 (s, 3H), 3.6 (t, 2H), 3.18 (s, 3H), 2.35 (m, 1H), 2.3 (m, 3H), 1.984 (dd, 2H), 1.65 (dd, 2H).

Workup

  1. temperaturethen warm
  2. stirringstir for 30 min
  3. customThe reaction was quenched with 25 mL of 10% HCl
  4. extractionextracted into 3×50 mL of ethyl acetate
  5. additionThe combined extracts were diluted with 50 mL of toluene
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customDrying under vacuum overnight

Sources & evidence

ORD record
ord-8b95acd2aab540b89b2dfb00caae9076
Source dataset
uspto-grants-2008_11
Patent number
US07452893B2

Reaction notes

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