1,2-Dichloroethane → HCID 59243637, compound

HRID 425014Notes

Reaction equation

HRID 425014 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:20]([OH:22])=[O:21])[CH2:10][CH2:11][O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:23]1(O)[CH2:27][CH2:26][CH2:25][CH2:24]1.C(Cl)CCl>C(Cl)Cl.CN(C1C=CN=CC=1)C.C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:20]([O:22][CH:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1)=[O:21])[CH2:10][CH2:11][O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 3

HCID 111,2-DichloroethaneHCID 7298CyclopentanolHCID 59243591HCID 59243591, compound

Product 1

HCID 59243637HCID 59243637, compoundYield 73%

Reagents, catalysts & solvents 3

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

Procedure

To a solution of N-(tert-butoxycarbonyl)-O-[tert-butyl(dimethyl)silyl]-D-homoserine (2.53 g, 7.6 mmol) in DCM (50 ml) at 0° C. was added cyclopentanol (1.39 ml, 15.3 ml, 2 eq), EDC (1.61 g, 8.4 mmol, 1.1 eq) and DMAP (0.093 g, 0.76 mmol, 0.1 eq). The reaction mixture was stirred for 16 hours at room temperature before evaporation under reduced pressure. The crude residue was dissolved in ethyl acetate (100 ml) and washed with 1M HCl, 1M Na2CO3 and brine. The organic layer was then dried over magnesium sulphate and evaporated under reduced pressure. The product was purified by column chromatography using ethyl acetate/heptane (1:4) to give 2.24 g, 73% yield of title compound.

Workup

  1. washwashed with 1M HCl, 1M Na2CO3 and brine
  2. dry with materialThe organic layer was then dried over magnesium sulphate
  3. customevaporated under reduced pressure
  4. customThe product was purified by column chromatography

Sources & evidence

ORD record
ord-160f9cbf268c460081a5beeed709804e
Source dataset
uspto-grants-2012_01
Patent number
US08106091B2

Reaction notes

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