Hydrochloric Acid → HCID 86705584, compound

HRID 2279602Notes

Reaction equation

HRID 2279602 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][C@H:7]2[C@@H:11]([OH:12])[CH2:10][N:9](C(OC(C)(C)C)=O)[CH2:8]2)=[CH:4][C:3]=1[F:22].Cl>CO>[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][C@H:7]2[CH2:8][NH:9][CH2:10][C@H:11]2[OH:12])=[CH:4][C:3]=1[F:22]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131733492HCID 131733492, compound

Product 1

HCID 86705584HCID 86705584, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 418 (0.560 g, 1.69 mmol) and MeOH (10 mL) was added a methanolic HCl solution (4 N, 5 mL). The mixture was stirred at RT for 3 h and the solvent was removed in vacuo. The residue was neutralized with satd. aq. NaHCO3 (20 mL) and extracted with DCM/IPA (3:1, 3×100 mL) to afford 0.35 g (90%) of cis-(±)-4-(4-chloro-3-fluorophenoxy)pyrrolidin-3-ol (420) as a yellow oil.

Workup

  1. customthe solvent was removed in vacuo
  2. extractionaq. NaHCO3 (20 mL) and extracted with DCM/IPA (3:1, 3×100 mL)

Sources & evidence

ORD record
ord-723d40bfac88402a966c1a1793591739
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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