Ammonia → HCID 67071573, compound

HRID 874231Notes

Reaction equation

HRID 874231 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:22])/[CH:5]=[CH:6]/[C:7]1[CH:8]=[C:9]2[C:18](=[CH:19][CH:20]=1)[O:17][C:12]1([CH2:16][CH2:15][NH:14][CH2:13]1)[CH2:11][C:10]2=[O:21].[CH:23](=O)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].N>C([O-])(O)=O.[Na+].O>[CH3:2][O:3][C:4](=[O:22])/[CH:5]=[CH:6]/[C:7]1[CH:8]=[C:9]2[C:18](=[CH:19][CH:20]=1)[O:17][C:12]1([CH2:16][CH2:15][N:14]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:13]1)[CH2:11][C:10]2=[O:21]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 240BenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 67071652HCID 67071652, compound2×

Product 1

HCID 67071573HCID 67071573, compoundYield 93.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A suspension of (±)-(E)-3-[4-oxo-spiro(chromane-2,3′-pyrrolidine)-6-yl]-acrylic acid methyl ester hydrochloride salt (440 mg, 1.36 mmol, Intermediate 1) in aqueous 10% NaHCO3 solution was extracted with DCM (3×10 ml). The organic phase was dried over Na2SO4 and evaporated. The resulting oil was dissolved in DCM (15 ml), treated with benzaldehyde (0.166 ml, 1.63 mmol) and NaBH(OAc)3 (433 mg, 2.04 mmol), and the resulting clear solution was stirred at RT for 2 h. Water was added to the mixture and the pH was brought to basic conditions with NH3. The mixture was extracted with DCM (3×10 ml). The organic layer was dried, evaporated, and the crude residue was purified by column chromatography (eluent: petroleum ether/EtOAc 7:3) to give (±)-(E)-3-[1′-benzyl-4-oxo-spiro(chromane-2,3′-pyrrolidine)-6-yl]-acrylic acid methyl ester (482 mg) as a light yellow solid.

Workup

  1. extractionwas extracted with DCM (3×10 ml)
  2. dry with materialThe organic phase was dried over Na2SO4
  3. customevaporated
  4. dissolutionThe resulting oil was dissolved in DCM (15 ml)
  5. extractionThe mixture was extracted with DCM (3×10 ml)
  6. customThe organic layer was dried
  7. customevaporated
  8. customthe crude residue was purified by column chromatography (eluent: petroleum ether/EtOAc 7:3)

Sources & evidence

ORD record
ord-639b959be1fe4899beefde90cb928bbe
Source dataset
uspto-grants-2015_03
Patent number
US08980877B2

Reaction notes

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