Hydrochloric Acid → HCID 67974870, compound

HRID 2168225Notes

Reaction equation

HRID 2168225 reaction equation
[F:1][C@@H:2]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][O:9][C:10]2[CH:11]=[C:12]([CH:18]=[CH:19][CH:20]=2)[C:13]([O:15]CC)=[O:14])[CH2:3]1.Cl>>[F:1][C@@H:2]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][O:9][C:10]2[CH:11]=[C:12]([CH:18]=[CH:19][CH:20]=2)[C:13]([OH:15])=[O:14])[CH2:3]1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 67974918HCID 67974918, compound

Product 1

HCID 67974870HCID 67974870, compound

Procedure

To the material of ethyl 3-({2-[(3R)-3-fluoro-1-pyrrolidinyl]ethyl}oxy)benzoate D48 (220 mg) was added HCl (0.3 ml, 9.87 mmol) at room temperature. The reaction was stirred at 100° for 2.5 hours. The mixture was concentrated in vacuo. To the residue was added 5 ml of ether and stirred 0.5 hours, filtered and the filtrate was evaporated in vacuo to give the expected product D52 in 160 mg. LCMS Retention time=0.90 mins, [M+H]+254 (5 min run)

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additionTo the residue was added 5 ml of ether
  3. stirringstirred 0.5 hours
  4. filtrationfiltered
  5. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-f87e5f26e314452a85c68921ed228775
Source dataset
uspto-grants-2015_06
Patent number
US09045485B2

Reaction notes

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