Piperidine → HCID 58981682, compound

HRID 268622Notes

Reaction equation

HRID 268622 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]#[C:10][CH2:11][CH2:12][O:13][S:14]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)(=[O:16])=[O:15])=[CH:5][CH:4]=1)=O.[NH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>C(Cl)Cl.C(O)(=O)C>[N:24]1([CH2:1][C:3]2[CH:8]=[CH:7][C:6]([C:9]#[C:10][CH2:11][CH2:12][O:13][S:14]([C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=3)(=[O:16])=[O:15])=[CH:5][CH:4]=2)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

7

Reactant 4

HCID 8082PiperidineHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 44243538HCID 44243538, compound

Product 1

HCID 58981682HCID 58981682, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of the product of Example 8 (2.0 g), piperidine (0.91 mL), and acetic acid (0.42 mL) in DCM (100 mL) was treated with sodium triacetoxyborohydride (1.95 g) at room temperature. After 16 h, the resulting mixture was treated with 10% aqueous sodium hydroxide (30 mL). The aqueous phase was extracted with DCM (2×300 mL). The combined organic phases were dried (magnesium sulfate) and concentrated under reduced pressure. The residue was diluted in DCM (100 mL) and passed through a pad of silica gel. The pad was washed with DCM (3×200 mL). The combined filtrate was concentrated under reduced pressure, giving the title compound as a brown oil (2.3 g).

Workup

  1. extractionThe aqueous phase was extracted with DCM (2×300 mL)
  2. dry with materialThe combined organic phases were dried (magnesium sulfate)
  3. concentrationconcentrated under reduced pressure
  4. additionThe residue was diluted in DCM (100 mL)
  5. washThe pad was washed with DCM (3×200 mL)
  6. concentrationThe combined filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-961486734a444b4b9a7f2050c7f522c4
Source dataset
uspto-grants-2008_11
Patent number
US07446104B2

Reaction notes

Loading…