(Diethylamino)sulfur trifluoride → Ethyl 3-(benzyl(cyclopentyl)amino)-2-fluoro-2-methylpropanoate

HRID 1880914Notes

Reaction equation

HRID 1880914 reaction equation
[CH2:1]([N:8]([CH:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1)[CH2:9][C:10](O)([CH3:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(S(F)(F)[F:29])CC>ClCCl>[CH2:1]([N:8]([CH:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1)[CH2:9][C:10]([F:29])([CH3:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 57955626Ethyl 3-(benzyl(cyclopentyl)amino)-2-hydroxy-2-methylpropanoate

Product 1

HCID 57955642Ethyl 3-(benzyl(cyclopentyl)amino)-2-fluoro-2-methylpropanoateYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To ethyl 3-(benzyl(cyclopentyl)amino)-2-hydroxy-2-methylpropanoate (4.2 g, 14 mmol) in 50 ml of dichlormethane at −78° C., was added DAST (2.7 ml, 21 mmol) dropwise. The reaction mixture was gradually warmed up to room temperature and stirred for 2 h. It was then diluted to dichloromethane, washed by NaHCO3, brine and water. Organic extract dried and concentrated to a residue, which was purified on silica gel column chromatographically (Hex/EtOAc=40:1 to 20:1) to give 3.5 g product (83%) as light yellow liquid. [M+H] calc'd for C18H26FNO2, 308; found 308.

Workup

  1. washwashed by NaHCO3, brine and water
  2. extractionOrganic extract
  3. customdried
  4. concentrationconcentrated to a residue, which
  5. customwas purified on silica gel column chromatographically (Hex/EtOAc=40:1 to 20:1)

Sources & evidence

ORD record
ord-8ea25b28561f45e2bd8e8936bc8a3048
Source dataset
uspto-grants-2012_11
Patent number
US08318727B2

Reaction notes

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