Ammonia → HCID 67071678, compound

HRID 874264Notes

Reaction equation

HRID 874264 reaction equation
[CH3:1][O:2][C:3](=[O:30])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[C:8]2[C:26](=[CH:27][CH:28]=1)[O:25][C:11]1([CH2:17][CH2:16][CH2:15][N:14]([C:18](OC(C)(C)C)=O)[CH2:13][CH2:12]1)[CH2:10][C:9]2=[O:29].C(=O)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=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:30])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[C:8]2[C:26](=[CH:27][CH:28]=1)[O:25][C:11]1([CH2:17][CH2:16][CH2:15][N:14]([CH2:18][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH2:13][CH2:12]1)[CH2:10][C:9]2=[O:29]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 240BenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 67071624HCID 67071624, compound2×

Product 1

HCID 67071678HCID 67071678, compoundYield 84.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A suspension of (±)-(E)-3-[4-oxo-spiro(chromane-2,4′-azepane)-6-yl]-acrylic acid methyl ester hydrochloride salt (500 mg, 1.43 mmol, Intermediate 3) in aqueous 10% NaHCO3 solution was extracted with DCM (3 times 10 ml). The organic phase was dried over Na2SO4 and evaporated. The resulting oil was dissolved in DCM (15 ml), treated with benzaldehyde (0.174 ml, 1.71 mmol) and NaBH(OAc)3 (455 mg, 2.14 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 pH value with NH3. The mixture was extracted with DCM (3 times 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-2,4′-azepane)-6-yl]-acrylic acid methyl ester (490 mg) as a light yellow solid.

Workup

  1. extractionwas extracted with DCM (3 times 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 times 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-399b1c23606d4406979fd1e29a7ee182
Source dataset
uspto-grants-2015_03
Patent number
US08980877B2

Reaction notes

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