m-Chloroperbenzoic acid → HCID 21701925, compound

HRID 1596467Notes

Reaction equation

HRID 1596467 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[C:12]([C:14]1[CH:40]=[CH:39][C:17]([O:18][CH2:19][CH:20]([OH:38])[CH2:21][N:22]2[CH2:29][CH:28]3[CH2:30][CH:24]([CH2:25][N:26]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:27]3)[CH2:23]2)=[CH:16][CH:15]=1)#[N:13]>C(Cl)Cl>[C:34]([O:33][C:31]([N:26]1[CH2:25][CH:24]2[CH2:30][CH:28]([CH2:29][N+:22]([CH2:21][CH:20]([OH:38])[CH2:19][O:18][C:17]3[CH:16]=[CH:15][C:14]([C:12]#[N:13])=[CH:40][CH:39]=3)([O-:9])[CH2:23]2)[CH2:27]1)=[O:32])([CH3:35])([CH3:36])[CH3:37]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 53796099Tert-butyl 7-[3-(4-cyanophenoxy)-2-hydroxypropyl]-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate

Product 1

HCID 21701925HCID 21701925, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

mCPBA (300 mg; 70%; 1.22 mmol) was added to a stirred solution of tert-butyl 7-[3-(4-cyanophenoxy)-2-hydroxypropyl]-3,7-diazabicyclo-[3.3.1]nonane-3-carboxylate (490 mg; 1.22 mmol; see Example 2 above) in DCM (10 mL) at 0° C. The reaction mixture was stirred for 1 h and then washed with NaHCO3 (aq.). The organic layer separated, dried, concentrated and subjected to column chromatography (DCM:MeOH; 19:1) to give the title compound in a 98% yield.

Workup

  1. washwashed with NaHCO3 (aq.)
  2. customThe organic layer separated
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-93ae0ea13ff742c0930abf0da7889470
Source dataset
uspto-grants-2001_09
Patent number
US06291475B1

Reaction notes

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