1-Methyl-3-pyrrolidinol → 1-Methyl-3-pyrrolidinyl 1-phenylcyclobutanecarboxylate Hydrochloride

HRID 1955269Notes

Reaction equation

HRID 1955269 reaction equation
[C:1]1([C:7]2([C:11]([Cl:13])=[O:12])[CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:14][N:15]1[CH2:19][CH2:18][CH:17]([OH:20])[CH2:16]1>CS(C)=O.C(O)(C(F)(F)F)=O>[ClH:13].[C:1]1([C:7]2([C:11]([O:20][CH:17]3[CH2:18][CH2:19][N:15]([CH3:14])[CH2:16]3)=[O:12])[CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 930741-Methyl-3-pyrrolidinolHCID 232948921-Phenylcyclobutanecarbonyl chloride

Product 1

HCID 702774921-Methyl-3-pyrrolidinyl 1-phenylcyclobutanecarboxylate Hydrochloride

Reagents, catalysts & solvents 1

HCID 20405524Dmso tfaSolvent

Procedure

The title compound was prepared in an analogous manner to that in Example 36 by reacting 1-phenylcyclobutanecarbonyl chloride with 1-methyl-3-hydroxypyrrolidine at 80° C. for 17 h. The yield was 1.1 g (67%); mp 153-155° C.; 1H NMR (DMSO-d6, 1% TFA) δ 1.83 (m, 1.5H), 1.96 (m, 1.5H), 2.17 (m, 0.5H), 2.38-2.51 (m, 2.5H), 2.64 (t, 1.5H), 2.73-2.92 (m, 4H), 2.97 (m, 0.5H), 3.06 (m, 0.5H), 3.32 (m, 0.5H), 3.54 (m, 1.5H), 3.76 (m, 0.5H), 5.26 (m, 1H), 7.23-7.39 (m, 5H). Anal. (C16H21NO2.HCl) C, H, N. The compound exists in two forms in DMSO-TFA solution.

Workup

  1. customat 80° C.
  2. customfor 17 h

Sources & evidence

ORD record
ord-366f1e414de54f66bcab6978e81cc744
Source dataset
uspto-grants-2000_09
Patent number
US06124354

Reaction notes

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