Hydrochloric Acid → (2R,4S)-2-(2-chlorophenoxymethyl)-4-fluoropyrrolidine

HRID 81394Notes

Reaction equation

HRID 81394 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][CH:20]=[CH:19][C:3]=1[O:4][CH2:5][C@H:6]1[CH2:10][C@H:9]([F:11])[CH2:8][N:7]1C(OC(C)(C)C)=O.Cl.C(=O)([O-])O.[Na+]>C1COCC1>[Cl:1][C:2]1[CH:22]=[CH:21][CH:20]=[CH:19][C:3]=1[O:4][CH2:5][C@H:6]1[CH2:10][C@H:9]([F:11])[CH2:8][NH:7]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 58483944tert-butyl (2R,4S)-2-(2-chlorophenoxymethyl)-4-fluoropyrrolidine-1-carboxylate

Product 1

HCID 58483921(2R,4S)-2-(2-chlorophenoxymethyl)-4-fluoropyrrolidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

7.7 2.5 g of tert-butyl (2R,4S)-2-(2-chlorophenoxymethyl)-4-fluoropyrrolidine-1-carboxylate are dissolved in 20 ml of THF and stirred at 80° C. for 2 h with 5 ml of ethanolic hydrochloric acid. After basic work-up using saturated sodium hydrogencarbonate solution, the organic phase is subjected to conventional work-up, and the residue obtained is purified by chromatography, giving 780 mg of (2R,4S)-2-(2-chlorophenoxymethyl)-4-fluoropyrrolidine as brown oil; Rt.: 0.700 min; [M+H]+230.2.

Workup

  1. customthe residue obtained
  2. customis purified by chromatography

Sources & evidence

ORD record
ord-8ec2275089e44ab09fec2df629e6515a
Source dataset
uspto-grants-2014_09
Patent number
US08846694B2

Reaction notes

Loading…