Ammonia → HCID 67071602, compound

HRID 874251Notes

Reaction equation

HRID 874251 reaction equation
[CH3:1][O:2][C:3](=[O:29])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[C:8]2[C:25](=[CH:26][CH:27]=1)[O:24][C:11]1([CH2:16][CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12]1)[CH2:10][C:9]2=[O:28].[CH:30](=O)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].N>C([O-])(O)=O.[Na+].O>[CH3:1][O:2][C:3](=[O:29])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[C:8]2[C:25](=[CH:26][CH:27]=1)[O:24][C:11]1([CH2:16][CH2:15][CH2:14][N:13]([CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH2:12]1)[CH2:10][C:9]2=[O:28]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 240BenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 67071461HCID 67071461, compound

Product 1

HCID 67071602HCID 67071602, compoundYield 64.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A suspension of Intermediate 2 (400 mg, 1.19 mmol) in NaHCO3 (10% aqueous solution) was extracted 3 times with DCM (10 ml). The organic phase was dried over Na2SO4 and evaporated. The resulting oil was dissolved in DCM (10 ml), treated with benzaldehyde (0.145 ml, 1.42 mmol) and NaBH(OAc)3 (383 mg, 1.78 mmol), and the resulting clear solution was stirred at RT for 2 h. Water was added to the mixture and the pH was adjusted to a basic value with NH3. The mixture was extracted 3 times with DCM (10 ml). The organic layer was dried, evaporated, and the crude residue was purified by column chromatography (eluent: DCM:MeOH 98:2) to give (±)-(E)-3-[1′-benzyl-4-oxo-spiro(chromane-2,3′-piperidine)-6-yl]-acrylic acid methyl ester (300 mg) as a light yellow solid.

Workup

  1. extractionwas extracted 3 times with DCM (10 ml)
  2. dry with materialThe organic phase was dried over Na2SO4
  3. customevaporated
  4. dissolutionThe resulting oil was dissolved in DCM (10 ml)
  5. extractionThe mixture was extracted 3 times with DCM (10 ml)
  6. customThe organic layer was dried
  7. customevaporated
  8. customthe crude residue was purified by column chromatography (eluent: DCM:MeOH 98:2)

Sources & evidence

ORD record
ord-9032ffd2f67e40d3b3afca66441c72aa
Source dataset
uspto-grants-2015_03
Patent number
US08980877B2

Reaction notes

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