Diisopropylamine → HCID 17773165, compound

HRID 635333Notes

Reaction equation

HRID 635333 reaction equation
C([N-]C(C)C)(C)C.[Li+].C(NC(C)C)(C)C.C([Li])CCC.[C:21]1(=[O:27])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.[C:28]([O:32][C:33]([N:35]1[CH2:43][CH2:42][CH:38]([C:39](O)=[O:40])[CH2:37][CH2:36]1)=[O:34])([CH3:31])([CH3:30])[CH3:29]>O1CCCC1.CO.C(Cl)(Cl)Cl>[C:28]([O:32][C:33]([N:35]1[CH2:43][CH2:42][CH:38]([C:39]([CH:22]2[CH2:23][CH2:24][CH2:25][CH2:26][C:21]2=[O:27])=[O:40])[CH2:37][CH2:36]1)=[O:34])([CH3:31])([CH3:30])[CH3:29]

Participants

9

Reactant 5

HCID 7912DiisopropylamineHCID 7967CyclohexanoneHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 2724682Lithium diisopropylamideHCID 178418339Butyllithium

Product 1

HCID 17773165HCID 17773165, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Lithium diisopropylamide solution prepared from diisopropylamine (2.8 ml) and 1 M n-butyl lithium (11 ml) in tetrahydrofuran (40 ml) was cooled to −78° C. and cyclohexanone (2.0 ml) was added. The mixture was stirred at −78° C. for 1 hour and 1-tert-butoxycarbonyl-4-imidazocarbonylpiperidine (4.8 g) prepared from N-tert-butoxycarbonylisonipecotic acid was added. The mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated and water was added to the obtained residue. The mixture was extracted with ethyl acetate and the extract was dried over anhydrous magnesium sulfate. The filtrate was concentrated under reduced pressure to give 3.8 g of an oily substance. The oil was subjected to silica gel column chromatography (eluent; chloroform:methanol=20:1) to give 2-((1-tert-butoxycarbonylpiperidin-4-yl)carbonyl)cyclohexanone, m.p. 71-72° C.

Workup

  1. additionwas added
  2. stirringThe mixture was stirred at room temperature for 1 hour
  3. concentrationThe reaction mixture was concentrated
  4. additionwater was added to the obtained residue
  5. extractionThe mixture was extracted with ethyl acetate
  6. dry with materialthe extract was dried over anhydrous magnesium sulfate
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customto give 3.8 g of an oily substance

Sources & evidence

ORD record
ord-fd7d763d9b8f4314abf58974788d4816
Source dataset
uspto-grants-2001_02
Patent number
US06187774B1

Reaction notes

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