4-Methylmorpholine → HCID 22458227, compound

HRID 1386797Notes

Reaction equation

HRID 1386797 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:24])[CH2:9][CH2:10][CH:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)=[CH:4][CH:3]=1.CN1CCOCC1>[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC.C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[O:24])[CH2:9][CH2:10][CH:11]2[CH2:12][CH2:13][N:14]([C:17]([O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:18])[CH2:15][CH2:16]2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 79724-MethylmorpholineHCID 53776264HCID 53776264, compound

Product 1

HCID 22458227HCID 22458227, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 500 mg (1.5 mmol) of 4-(3-(4-fluorophenyl)-3-(RS)-hydroxypropyl)-1-(t-butoxycarbonyl) piperidine (from EXAMPLE 188, Step B), 351 mg (3.0 mmol) of 4-(methyl)morpholine and 800 mg of 4 A molecular sieves in 10 _mL of CH2Cl2 at 0° C. was treated with 35 mg (0.1 mmol) of tetrapropylammonium perruthenate. The cooling bath was removed and the mixture was stirred at rt for 1 h. The mixture was filtered and the filtrate was concentrated. Flash chromatography on 15 g of silica gel using 3:1 v/v hexanes/ether afforded 386 mg (78%) of the title compound: 1H NMR (500 MHz, CDCl3) δ 1.10-1.19 (m, 2H), 1.43-1.49 (m, 1H), 1.45 (s, 9H), 1.58-1.70 (4H), 2.65-2.70 (m, 2H), 2.70 (t, J=7.5, 2H), 4.054.1 1 (m, 2H), 7.11-7.15 (m, 21), 7.97-8.00 (m, 2H).

Workup

  1. customThe cooling bath was removed
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-7942ff27c7b440c5902a1a3def724272
Source dataset
uspto-grants-2001_07
Patent number
US06265434B1

Reaction notes

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