Piperidine → HCID 10066807, compound

HRID 1179385Notes

Reaction equation

HRID 1179385 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][CH:12]([CH:15]=O)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1)=O.[NH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.C(O[BH-](O[C:33](=O)[CH3:34])OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>C(Cl)Cl.C(O)(=O)C>[N:17]1([CH2:1][C:3]2[CH:8]=[CH:7][C:6]([N:9]3[CH2:14][CH2:13][CH:12]([CH2:15][N:9]4[CH2:34][CH2:33][CH2:4][CH2:5][CH2:6]4)[CH2:11][CH2:10]3)=[CH:5][CH:4]=2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

7

Reactant 4

HCID 8082PiperidineHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 58978040HCID 58978040, compound

Product 1

HCID 10066807HCID 10066807, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of the product of Example 21 (194.6 mg), piperidine (196 μL), and acetic acid (114 μL) in DCM (5 mL) was treated with sodium triacetoxyborohydride (570 mg). After 16 h, the resulting mixture was treated with 10% sodium hydroxide (10 mL), and the mixture was extracted with DCM (3×10 mL). The combined organic phases were dried (sodium sulfate) and concentrated under reduced pressure. Chromatography of the residue on silica gel (1-7% 2 M methanolic ammonia/DCM) gave the title compound (193.1 mg).

Workup

  1. extractionthe mixture was extracted with DCM (3×10 mL)
  2. dry with materialThe combined organic phases were dried (sodium sulfate)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-beb8387544134020aadbe7804f806108
Source dataset
uspto-grants-2007_10
Patent number
US07279491B2

Reaction notes

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