Acetic Acid → HCID 68468405, compound

HRID 2235273Notes

Reaction equation

HRID 2235273 reaction equation
[Cl:1][C:2]1[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[C:3]=1[CH2:4][C@H:5]([C:9](=[O:28])[N:10]1[C@@H:14](C2C=CC=CC=2)[C@@H:13]([C:21]2C=C[CH:24]=[CH:23][CH:22]=2)O[C:11]1=O)[CH2:6]C=O.C1(N)CCCCC1.CC(O)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C1COCC1>[Cl:1][C:2]1[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[C:3]=1[CH2:4][C@H:5]1[CH2:6][CH2:11][N:10]([CH:14]2[CH2:13][CH2:21][CH2:22][CH2:23][CH2:24]2)[C:9]1=[O:28]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7965CyclohexylamineHCID 5049666Sodium triacetoxyborohydrideHCID 86624441HCID 86624441, compound

Product 1

HCID 68468405HCID 68468405, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve (S)-3-(2-Chloro-6-fluoro-benzyl)-4-oxo-4-((4S,5R)-2-oxo-4,5-diphenyl-oxazolidin-3-yl)-butyraldehyde (Preparation 85) (0.384 g, 0.825 mmol) in THF (20 mL). Add cyclohexanamine (0.098 g, 0.99 mmol) and AcOH (0.049 g, 0.82 mmol). Stir the mixture for one hour and then add NaBH(OAc)3 (0.262 g, 1.24 mmol). Stir the reaction mixture for 24 hours until LC-MS shows the starting material has been gone. Add water (20 mL) and extract the aqueous with CH2Cl2 (3×50 mL). Combine the organic layers and dry over Na2SO4. Concentrate and purify by chromatography (Silica gel) to afford (S)-3-(2-Chloro-6-fluorobenzyl)-1-cyclohexylpyrrolidin-2-one (0.172 g, 67%). MS (APCI-pos mode) m,/z (rel intensity) 310 (100), 312 (35).

Workup

  1. stirringStir the reaction mixture for 24 hours until LC-MS
  2. extractionAdd water (20 mL) and extract the aqueous with CH2Cl2 (3×50 mL)
  3. dry with materialCombine the organic layers and dry over Na2SO4
  4. concentrationConcentrate
  5. custompurify by chromatography (Silica gel)

Sources & evidence

ORD record
ord-b65de40af0e6476fbcea1a3fcad3068c
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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