Acetic Acid → HCID 67265876, compound

HRID 1686063Notes

Reaction equation

HRID 1686063 reaction equation
C([C@@H]1COC(=O)[N:9]1[C:14](=[O:30])[CH:15]([CH2:19][C:20]1[C:25]([Cl:26])=[CH:24][C:23]([O:27][CH3:28])=[CH:22][C:21]=1[Cl:29])[CH2:16][CH:17]=C)C1C=CC=CC=1.N[N:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1>[ClH:26].[Cl:26][C:25]1[CH:24]=[C:23]([O:27][CH3:28])[CH:22]=[C:21]([Cl:29])[C:20]=1[CH2:19][C@@H:15]1[CH2:16][CH2:17][N:9]([N:32]2[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)[C:14]1=[O:30]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 166581-AminopiperidineHCID 5049666Sodium triacetoxyborohydrideHCID 86635716HCID 86635716, compound

Product 1

HCID 67265876HCID 67265876, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add to a solution of (R)-4-((R)-4-benzyl-3-[2-(4-methoxy-2,6-dichloro-benzyl)-pent-4-enoyl]-oxazolidin-2-one (0.90 g, 2 mmol) in THF (20 mL) at room temperature 1-amino piperidine (0.40 g, 4 mmol) and acetic acid (0.2 mL). Stir the reaction at room temperature for 20 minutes and add sodium triacetoxy borohydride (1.69 g, 8 mmol) and continue stirring at room temperature for 12 h. Partition the mixture between ethyl acetate (20 mL) and water (20 mL). Separate the organic layer, wash three times with water (15 mL each) and then with brine (15 mL). After drying the organic layer over sodium sulfate, filter and concentrate under vacuum. Purify the residue by silica gel chromatography with 2:3 ethyl acetate/hexane to afford the free base of the title compound and then treat with 1 M HCl in ether to afford 0.34 g (43%): MS (m/z): 357 (M+).

Workup

  1. customthe reaction at room temperature for 20 minutes
  2. stirringcontinue stirring at room temperature for 12 h
  3. customPartition the mixture between ethyl acetate (20 mL) and water (20 mL)
  4. customSeparate the organic layer
  5. washwash three times with water (15 mL each)
  6. dry with materialAfter drying the organic layer over sodium sulfate
  7. filtrationfilter
  8. concentrationconcentrate under vacuum
  9. customPurify the residue by silica gel chromatography with 2:3 ethyl acetate/hexane

Sources & evidence

ORD record
ord-0b0d68c1c9af47fd8f7b3de023aba981
Source dataset
uspto-grants-2012_04
Patent number
US08148534B2

Reaction notes

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