Methanol → HCID 70153550, compound

HRID 2296821Notes

Reaction equation

HRID 2296821 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH:15]3[CH:19]([CH2:20][CH2:21][OH:22])[CH2:18][NH:17][CH2:16]3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.CCN(CC)CC.[CH:30]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:33]=[CH:32][C:31]=1C(Cl)=O.[CH3:43][OH:44]>C(Cl)Cl>[C:38]1([C:43]([N:17]2[CH2:18][CH:19]([CH2:20][CH2:21][OH:22])[CH:15]([CH2:14][N:11]3[CH2:12][CH2:13][CH:8]([C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=4)[CH2:9][CH2:10]3)[CH2:16]2)=[O:44])[C:39]2[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:35]=[CH:36][CH:37]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 752462-Naphthoyl chlorideHCID 70154819HCID 70154819, compound

Product 1

HCID 70153550HCID 70153550, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.63 g (2.15 mmol) of 3-(RS)-(4-(4-fluorophenyl) piperidinylmethyl)-4-(SR)-hydroxyethylpyrrolidine and 0.6 mL (4.3 mmol) of Et3N in 20 mL of CH2Cl2 at 0° C. was added 0.32 mL (2.15 mmol) of 2-naphthoyl chloride and the reaction mixture was stirred for 1.2 h. To the reaction mixture was added 0.5 mL of MeOH and the reaction mixture was stirred 18 h at rt. The reaction mixture was concentrated and the residue was purified by chromatography (silica, acetone: hexanes, 1:2 to 1:1) to give 0.63 g of the title compound.

Workup

  1. stirringthe reaction mixture was stirred 18 h at rt
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was purified by chromatography (silica, acetone: hexanes, 1:2 to 1:1)

Sources & evidence

ORD record
ord-c5761387e9144905be8895c4d9d0ea6a
Source dataset
uspto-grants-2002_12
Patent number
US06489354B1

Reaction notes

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