Triethylamine → HCID 86761380, compound

HRID 1668394Notes

Reaction equation

HRID 1668394 reaction equation
[OH:1][CH:2]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:6][CH:5]=1)[CH3:3].C(N(CC)CC)C.[CH3:27][S:28](Cl)(=[O:30])=[O:29]>ClCCl>[CH3:27][S:28]([O:1][CH:2]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][NH:12][C:13]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:19])=[CH:6][CH:5]=1)[CH3:3])(=[O:30])=[O:29]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86761381HCID 86761381, compound

Product 1

HCID 86761380HCID 86761380, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

tert-Butyl [2-[4-(1-hydroxyethyl)phenyl]ethyl]carbamate (606 mg) was dissolved in dichloromethane (20 ml), triethylamine (0.38 ml) and then methanesulfonyl chloride (0.195 ml) were added at 0° C., and the mixture was stirred for 4 hr. The reaction mixture was diluted with dichloromethane, and washed with saturated aqueous sodium hydrogen carbonate solution and then saturated brine. The organic layer was dried over sodium sulfate, and the solvent was evaporated under reduced pressure to give 1-[4-[2-[(tert-butoxycarbonyl)amino]ethyl]phenyl]ethyl methanesulfonate. The obtained compound, (3S)-3-fluoropyrrolidine hydrochloride (287 mg) and N,N-diisopropylethylamine (1.18 g) were mixed with DMF (10 ml), and the mixture was stirred at 50° C. for 48 hr. The reaction mixture was diluted with ethyl acetate, and washed with water and then saturated brine. The organic layer was dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1 (volume ratio)→ethyl acetate→ethyl acetate:methanol=9:1 (volume ratio)) to give tert-butyl [2-[4-[1-[(3S)-3-fluoropyrrolidin-1-yl]ethyl]phenyl]ethyl]carbamate (133 mg) as a crude oil.

Workup

  1. washwashed with saturated aqueous sodium hydrogen carbonate solution
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-8dbc629683124849880663f5be8205b4
Source dataset
uspto-grants-2011_08
Patent number
US07989445B2

Reaction notes

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