(Diethylamino)sulfur trifluoride → Ethyl 2-((benzyl(cyclopentyl)amino)methyl)-2-fluorobutanoate

HRID 1880934Notes

Reaction equation

HRID 1880934 reaction equation
[CH2:1]([N:8]([CH2:14][C:15](O)([CH2:21][CH3:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(S(F)(F)[F:30])CC>ClCCl>[CH2:1]([N:8]([CH2:14][C:15]([F:30])([CH2:21][CH3:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 57955651Ethyl 2-((benzyl(cyclopentyl)amino)methyl)-2-hydroxybutanoate

Product 1

HCID 57955532Ethyl 2-((benzyl(cyclopentyl)amino)methyl)-2-fluorobutanoateYield 75.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To ethyl 2-((benzyl(cyclopentyl)amino)methyl)-2-hydroxybutanoate (2.9 g, 9.1 mmol) in 30 ml of dichlormethane at −78° C., was added DAST (2.4 ml, 18 mmol) dropwise. The reaction mixture was gradually warmed up to room temperature and stirred for 1 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 2.2 g product (75%) as light yellow liquid. [M+H] calc'd for C19H28FNO2, 322; found 322.

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-acd205d4b9cc4f199a3830350acbb541
Source dataset
uspto-grants-2012_11
Patent number
US08318727B2

Reaction notes

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