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Acetyl chloride → 1-{(R)-2-[2-(3-fluorophenyl)ethyl]pyrrolidin-1-yl}ethanone

HRID 928085
Notes
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Reaction equation

HRID 928085 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].C(N(C(C)C)CC)(C)C.[F:14][C:15]1[CH:16]=[C:17]([CH2:21][CH2:22][C@@H:23]2[CH2:27][CH2:26][CH2:25][NH:24]2)[CH:18]=[CH:19][CH:20]=1>C(Cl)Cl>[F:14][C:15]1[CH:16]=[C:17]([CH2:21][CH2:22][C@@H:23]2[CH2:27][CH2:26][CH2:25][N:24]2[C:1](=[O:3])[CH3:2])[CH:18]=[CH:19][CH:20]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 86713377(R)-2-[2-(3-fluorophenyl)-ethyl]pyrrolidine2×

Product 1

HCID 709837131-{(R)-2-[2-(3-fluorophenyl)ethyl]pyrrolidin-1-yl}ethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetyl chloride (0.29 ml) was added to a solution of N,N-diisopropyl-N-ethylamine (0.71 ml) and (R)-2-[2-(3-fluorophenyl)ethyl]-pyrrolidine (Intermediate 233, 0.39 g) in DCM (30 ml) and the mixture was stirred for 1.5 hours. The mixture was washed with 1M HCl, dried (MgSO4) and filtered. The filtrate was evaporated to dryness to give 1-{(R)-2-[2-(3-fluorophenyl)ethyl]-pyrrolidin-1-yl}ethanone (0.48 g) as an oil.

Workup

  1. washThe mixture was washed with 1M HCl
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-f6d27880c62e4827927dd500f368737a
Source dataset
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09290472B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes