(Diethylamino)sulfur trifluoride → HCID 58674941, compound

HRID 2244400Notes

Reaction equation

HRID 2244400 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14]O)[N:9]=1)([CH3:4])([CH3:3])[CH3:2].C(N(S(F)(F)[F:23])CC)C>ClCCl>[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][F:23])[N:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 19349090Tert-butyl (6-(hydroxymethyl)pyridin-2-yl)carbamate

Product 1

HCID 58674941HCID 58674941, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (6-hydroxymethyl-pyridin-2-yl)-carbamic acid tert-butyl ester (prepared as illustrated in example 135) (0.20 g, 0.90 mmol) in dichloromethane (20.00 ml) was cooled under argon to 0° C. and (diethylamino)sulfur trifluoride (DAST) (0.20 g, 1.25 mmol) was added dropwise. The resulting solution was stirred at room temperature for 30 min, then quenched by pouring the reaction mixture onto saturated sodium bicarbonate. The organic phase was separated, dried over sodium sulphate and evaporated to a orange oil, which was purified by flash chromatography (dichloromethane/ether) to yield (6-fluoromethyl-pyridin-2-yl)-carbamic acid tert-butyl ester (0.10 g, 51%) as a colorless oil, MS (ISP): m/e=211.3 (M+H+).

Workup

  1. customquenched
  2. additionby pouring the reaction mixture onto saturated sodium bicarbonate
  3. customThe organic phase was separated
  4. dry with materialdried over sodium sulphate
  5. customevaporated to a orange oil, which
  6. customwas purified by flash chromatography (dichloromethane/ether)

Sources & evidence

ORD record
ord-eb4e21a2b19f4f59b89abb0ca66a9cd2
Source dataset
uspto-grants-2010_03
Patent number
US07678815B2

Reaction notes

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