Piperidine → HCID 58710084, compound

HRID 2375837Notes

Reaction equation

HRID 2375837 reaction equation
[CH2:1]([O:8][C:9](=[O:15])[C:10]([CH3:14])([CH3:13])[CH:11]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH2:1]([O:8][C:9](=[O:15])[C:10]([CH3:14])([CH3:13])[CH2:11][N:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 5049666Sodium triacetoxyborohydrideHCID 11171763benzyl 2-formyl-2-methylpropanoate

Product 1

HCID 58710084HCID 58710084, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of benzyl-2,2-dimethyl-3-oxopropanoate (200 mg, 1.0 mmol) in DCM (30 mL) were added piperidine (0.10 mL, 1.1 mmol) and sodium triacetoxyborohydride (400 mg, 2.0 mmol). The reaction mixture was left to stir at rt for 16 h. The mixture was partitioned between DCM and water and treated with saturated NaHCO3. The combined organic extracts were dried over Na2SO4 and concentrated in vacuo. Purification via silica gel chromatography (5% EtOAc in Hexane) afforded the title compound as a yellow oil. MS (ES+): m/z: 276.18 (100) [MH+]. HPLC: tr=1.97 min (ZQ2000: polar—5 min). 1H NMR (400 MHz, CDCl3): δ=1.17 (s, 6H), 1.28-1.37 (m, 2H), 1.40-1.46 (m, 4H), 2.34-2.36 (m, 4H), 2.44 (s, 2H), 5.09 (s, 2H), 7.25-7.34 (m, 5H).

Workup

  1. waitThe reaction mixture was left
  2. customThe mixture was partitioned between DCM and water
  3. additiontreated with saturated NaHCO3
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customPurification via silica gel chromatography (5% EtOAc in Hexane)

Sources & evidence

ORD record
ord-9ec09c3154e94e40a3bc51b4bd1a3ac5
Source dataset
uspto-grants-2008_12
Patent number
US07465726B2

Reaction notes

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