Acetic Acid → HCID 67071602, compound

HRID 874259Notes

Reaction equation

HRID 874259 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:23])/[CH:5]=[CH:6]/[C:7]1[CH:8]=[C:9]2[C:19](=[CH:20][CH:21]=1)[O:18][C:12]1([CH2:17][CH2:16][CH2:15][NH:14][CH2:13]1)[CH2:11][C:10]2=[O:22].CC(O)=O.[CH:28](=O)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[CH3:2][O:3][C:4](=[O:23])/[CH:5]=[CH:6]/[C:7]1[CH:8]=[C:9]2[C:19](=[CH:20][CH:21]=1)[O:18][C:12]1([CH2:17][CH2:16][CH2:15][N:14]([CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:13]1)[CH2:11][C:10]2=[O:22]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 67071454HCID 67071454, compound

Product 1

HCID 67071602HCID 67071602, compoundYield 93.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(−)-(E)-3-[4-Oxo-spiro(chromane-2,3′-piperidine)-6-yl]-acrylic acid methyl ester hydrochloride (505 mg, 1.49 mmol) was suspended in DCM (50 ml). TEA (0.208 ml, 1.49 mmol) was added and the pH was adjusted to 5 with AcOH. Benzaldehyde (190 mg, 1.794 mmol) and NaBH(OAc)3 (475 mg, 2.24 mmol) were added and the mixture was stirred at RT for 3 h. The resulting solution was washed with 5% NaHCO3 and brine, then dried over Na2SO4 and evaporated to dryness. The crude product was purified by column chromatography (eluent:petroleum ether:EtOAc 9:1 to 7:3) to give (−)-(E)-3-[1′-benzyl-4-oxo-spiro(chromane-2,3′-piperidine)-6-yl]-acrylic acid methyl ester (547 mg).

Workup

  1. washThe resulting solution was washed with 5% NaHCO3 and brine
  2. dry with materialdried over Na2SO4
  3. customevaporated to dryness
  4. customThe crude product was purified by column chromatography (eluent:petroleum ether:EtOAc 9:1 to 7:3)

Sources & evidence

ORD record
ord-48dbafd031334dc8b0fa77b7bfc0a107
Source dataset
uspto-grants-2015_03
Patent number
US08980877B2

Reaction notes

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