Bromocyclopentane → HCID 178474767, compound

HRID 1260508Notes

Reaction equation

HRID 1260508 reaction equation
[OH:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][C@H:7]2[CH2:12][O:11][C@@H:10]([CH2:13][CH2:14][CH2:15][NH:16][C:17](=[O:19])[CH3:18])[O:9][CH2:8]2)=[CH:4][CH:3]=1.[CH:22]1(Br)[CH2:26][CH2:25][CH2:24][CH2:23]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH:22]1([O:1][C:2]2[CH:3]=[CH:4][C:5]([O:6][C@H:7]3[CH2:8][O:9][C@@H:10]([CH2:13][CH2:14][CH2:15][NH:16][C:17](=[O:19])[CH3:18])[O:11][CH2:12]3)=[CH:20][CH:21]=2)[CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 8728Bromocyclopentane2×HCID 10796Cesium carbonate2×HCID 178474769HCID 178474769, compound

Product 1

HCID 178474767HCID 178474767, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

cis-N-{3-[5-(4-Hydroxyphenoxy)-[1,3]dioxan-2-yl]propyl}acetamide (18.6 mg, 0.063 mmol), cyclopentyl bromide (11.3 mg, 0.076 mmol) and cesium carbonate (24.6 mg, 0.076 mmol) were stirred in 3 ml of DMF at room temperature for 3 h. Addition of 11 mg of cyclopentyl bromide and 20 mg of cesium carbonate on each of two occasions was followed by stirring for a total of 8 h and concentrating, and the residue was taken up in ethyl acetate and water. The organic phase was separated off, concentrated and purified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA). Yield: 8.5 mg (37%), M+H+: 364.22.

Workup

  1. concentrationconcentrating
  2. customThe organic phase was separated off
  3. concentrationconcentrated
  4. custompurified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA)

Sources & evidence

ORD record
ord-d335f8f5d76340829cad87c1d354d397
Source dataset
uspto-grants-2013_06
Patent number
US08470841B2

Reaction notes

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