(Diethylamino)sulfur trifluoride → Tert-butyl 2-fluoro-2-methylcyclopentylcarbamate

HRID 1408940Notes

Reaction equation

HRID 1408940 reaction equation
C(N(S(F)(F)[F:7])CC)C.O[C:11]1([CH3:24])[CH2:15][CH2:14][CH2:13][CH:12]1[NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20]>ClCCl>[F:7][C:11]1([CH3:24])[CH2:15][CH2:14][CH2:13][CH:12]1[NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20]

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 59281702Tert-butyl 2-hydroxy-2-methylcyclopentylcarbamate

Product 1

HCID 68291793Tert-butyl 2-fluoro-2-methylcyclopentylcarbamateYield 48.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(Diethylamino)sulphur trifluoride (2.75 mL, 20.84 mmol) was added to a solution of tert-butyl 2-hydroxy-2-methylcyclopentylcarbamate (2.243 g, 10.42 mmol, from Step 3) in dichloromethane (40 mL) at −78° C. under nitrogen. After 4 h at −78° C., the mixture was quenched with saturated sodium bicarbonate, allowed to warm to room temperature, and extracted with dichloromethane. The dichloromethane phase was concentrated and purified by silica gel chromatography, eluting with 0 to 50% ethyl acetate in hexanes, to give tert-butyl 2-fluoro-2-methylcyclopentylcarbamate as brown oil (1.095 g, 48% yield). 1H NMR analysis indicated approximately 3.5:1 mixture of two diastereomers.

Workup

  1. customthe mixture was quenched with saturated sodium bicarbonate
  2. extractionextracted with dichloromethane
  3. concentrationThe dichloromethane phase was concentrated
  4. custompurified by silica gel chromatography
  5. washeluting with 0 to 50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-a62e9107d1f64a96ab0ce6fd4b67a1b5
Source dataset
uspto-grants-2014_12
Patent number
US08921368B2

Reaction notes

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