Cyclopentanol → HCID 59622363, compound

HRID 1622962Notes

Reaction equation

HRID 1622962 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]([CH3:14])([C:11]([OH:13])=[O:12])[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:15]1(O)[CH2:19][CH2:18][CH2:17][CH2:16]1.CCN=C=NCCCN(C)C>C(Cl)Cl.CN(C1C=CN=CC=1)C.CCOC(C)=O>[C:1]([O:5][C:6]([NH:8][C:9]([CH3:14])([C:11]([O:13][CH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1)=[O:12])[CH3:10])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 3

HCID 7298CyclopentanolHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 2733845N-((1,1-dimethylethoxy)carbonyl)-2-methyl-alanine

Product 1

HCID 59622363HCID 59622363, compoundYield 20%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-(tert-butoxycarbonyl)-2-methylalanine (1.00 g, 4.92 mmol) in DCM (10 ml) at 0° C. was added cyclopentanol (0.83 ml, 9.84 mmol), EDCI (1.06 g, 5.42 mmol) and finally DMAP (60 mg, 0.49 mmol). The reaction mixture was warmed to RT and stirred for 18 hours. The DCM was removed in vacuo to give a clear oil. The crude residue was dissolved in EtOAc (100 ml) and washed with water, 1 M NaHCO3 and brine. The organic phase was dried (MgSO4) and concentrated in vacuo. The crude extract was purified by column chromatography (10% EtOAc in heptane) to yield the desired product as a clear oil (0.254 g, 20% yield).

Workup

  1. customThe DCM was removed in vacuo
  2. customto give a clear oil
  3. washwashed with water, 1 M NaHCO3 and brine
  4. dry with materialThe organic phase was dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. extractionThe crude extract
  7. customwas purified by column chromatography (10% EtOAc in heptane)

Sources & evidence

ORD record
ord-daa5090c366d4c4fa61132f24c9f7660
Source dataset
uspto-grants-2014_07
Patent number
US08778953B2

Reaction notes

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