4-Fluorobenzaldehyde → HCID 67071636, compound

HRID 874248Notes

Reaction equation

HRID 874248 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].[F:23][C:24]1[CH:31]=[CH:30][C:27]([CH:28]=O)=[CH:26][CH:25]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C([O-])(O)=O.[Na+]>[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]([CH2:28][C:27]3[CH:30]=[CH:31][C:24]([F:23])=[CH:25][CH:26]=3)[CH2:13]1)[CH2:11][C:10]2=[O:21]

Participants

5

Reactant 3

HCID 680234-FluorobenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 67071652HCID 67071652, compound

Product 1

HCID 67071636HCID 67071636, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

A suspension of Intermediate 1 (250 mg, 0.77 mmol) in aqueous 10% NaHCO3 solution was extracted with DCM (3×10 ml). The organic phase was dried over Na2SO4 and evaporated. The resulting solid was dissolved in DCM (10 ml), treated with 4-fluoro-benzaldehyde (0.090 ml, 0.85 mmol) and NaBH(OAc)3 (245 mg, 1.15 mmol) as described in Example 2, Step A, to give (±)-(E)-3-[1′-(4-fluoro-benzyl)-4-oxo-spiro(chromane-2,3′-pyrrolidine)-6-yl]-acrylic acid methyl ester (300 mg, 0.76 mmol, 99%) as a light brown 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 solid was dissolved in DCM (10 ml)

Sources & evidence

ORD record
ord-24f69e9b3c7b43cb9ee6c9cf23a2980b
Source dataset
uspto-grants-2015_03
Patent number
US08980877B2

Reaction notes

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