Methallyl alcohol → HCID 59527702, compound

HRID 2189973Notes

Reaction equation

HRID 2189973 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.CN(C)CCCN=C=NCC.[CH3:29][C:30](=[CH2:33])[CH2:31]O>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:31][C:30](=[CH2:29])[CH2:33][O:15][C:14]([CH:11]1[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][CH2:10]1)=[O:16]

Participants

6

Reactant 3

HCID 10557Methallyl alcoholHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 59527702HCID 59527702, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Under inert condition a 500 mL round bottom flask with a magnetic stirrer was charged with 6.87 g (30 mmol) of 1-tert.-butyloxycarbonyl-piperidine-4-carboxylic acid, 110 mg (0.09 mmol) DMAP and 11.5 g (60 mmol) 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide, hydrochloride and 150 mL DCM. To the light yellow solution 3.25 g (45 mmol) 2-methyl-2-propen-1-ol was added. The reaction mixture was stirred over night at room temperature. The mixture was concentrated under vacuum, isolute-HM-N was added and evaporated to dryness. The residue was purified over silica eluting with heptane and ethyl acetate to yield after evaporation of the product containing fractions 7.3 g (86%) of the title compound as colourless oil. MS ISP (m/e): 306.2 [(M+H)+].

Workup

  1. concentrationThe mixture was concentrated under vacuum, isolute-HM-N
  2. additionwas added
  3. customevaporated to dryness
  4. customThe residue was purified over silica eluting with heptane and ethyl acetate
  5. customto yield
  6. customafter evaporation of the product
  7. additioncontaining fractions 7.3 g (86%) of the title compound as colourless oil

Sources & evidence

ORD record
ord-1ec3b65dfa1e4ad8a30d84251842d32d
Source dataset
uspto-grants-2012_12
Patent number
US08324250B2

Reaction notes

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