Acetic Acid → HCID 57425834, compound

HRID 1727307Notes

Reaction equation

HRID 1727307 reaction equation
[F:1][C@H:2]1[C@H:5]([CH2:6][O:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:4][C:3]1=O.[CH2:16]([NH2:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].CC(O)=O>ClCCCl>[CH2:16]([NH:23][CH:3]1[CH2:4][CH:5]([CH2:6][O:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:2]1[F:1])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7504BenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 66739515HCID 66739515, compound

Product 1

HCID 57425834HCID 57425834, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

In a 25 mL flask with trans-2-fluoro-3-(benzyloxymethyl)cyclobutanone (0.20 g, 0.96 mmol) inside, dry 1,2-DCE 3.4 mL was added under argon to give a colorless solution. To this, benzylamine (0.11 mL, 1.01 mmol) was added to give still a colorless solution. After stirring for 5 min, sodium triacetoxyborohydride (0.29 g, 1.37 mmol) was added all at once to give a white emulsion. Then AcOH (0.06 mL, 1.05 mmol) was added drop by drop. After 5 min, it gave a yellow solution and this was left stirring for 2 hr and then the reaction was quenched by sat. NaHCO3. The organic phase was separated and the aqueous phase was extracted with EtOAc twice. The combined organic phase was dried over MgSO4 and the crude product was purified by silica gel flash chromatography (Hexane:EtOAc=3:1) to give 0.19 g (65%, Rf=0.18) of the product. 1H NMR (CDCl3, 600 MHz): δ 1.81-1.95 (m, 3H), 2.80-2.89 (m, 1H), 3.46-3.56 (m, 3H), 3.76-3.84 (m, 3H), 4.51-4.55 (m, 2H), 4.89-5.00 (td, 1H, J=54.6, 4.8), 7.25-7.37 (m, 10H).

Workup

  1. customto give a colorless solution
  2. customto give still a colorless solution
  3. customto give a white emulsion
  4. waitAfter 5 min
  5. customit gave a yellow solution
  6. waitthis was left
  7. stirringstirring for 2 hr
  8. customthe reaction was quenched by sat. NaHCO3
  9. customThe organic phase was separated
  10. extractionthe aqueous phase was extracted with EtOAc twice
  11. dry with materialThe combined organic phase was dried over MgSO4
  12. customthe crude product was purified by silica gel flash chromatography (Hexane:EtOAc=3:1)
  13. customto give 0.19 g (65%, Rf=0.18) of the product

Sources & evidence

ORD record
ord-32753b2282a54c6fad3b5c6904f681a6
Source dataset
uspto-grants-2009_02
Patent number
US07495006B2

Reaction notes

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