m-Chloroperbenzoic acid → 4-(1-((1-Hydroxy-4-adamantyloxy)carbonyl)pyrrolidin-3-yl)pyridine 1-oxide

HRID 1752321Notes

Reaction equation

HRID 1752321 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH:7]2[CH2:11][CH2:10][N:9]([C:12]([O:14][CH:15]3[CH:22]4[CH2:23][C:18]5([OH:25])[CH2:19][CH:20]([CH2:24][CH:16]3[CH2:17]5)[CH2:21]4)=[O:13])[CH2:8]2)=[CH:3][CH:2]=1.C1C=C(Cl)C=C(C(OO)=[O:34])C=1>C(Cl)Cl.CO>[OH:25][C:18]12[CH2:23][CH:22]3[CH2:21][CH:20]([CH2:24][CH:16]([CH:15]3[O:14][C:12]([N:9]3[CH2:10][CH2:11][CH:7]([C:4]4[CH:5]=[CH:6][N+:1]([O-:34])=[CH:2][CH:3]=4)[CH2:8]3)=[O:13])[CH2:17]1)[CH2:19]2

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 498355471-Hydroxy-4-adamantyl 3-(pyridin-4-yl)pyrrolidine-1-carboxylate

Product 1

HCID 498355484-(1-((1-Hydroxy-4-adamantyloxy)carbonyl)pyrrolidin-3-yl)pyridine 1-oxideYield 108.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 1-hydroxy-4-adamantyl 3-(pyridin-4-yl)pyrrolidine-1-carboxylate (476 mg, 1.39 mmol) in CH2Cl2 (50 mL) was cooled in an ice bath and solid m-CPBA (˜70%, 342 mg, ˜1.4 mmol) was added. The ice bath was allowed to melt and the mixture was stirred at rt for 2 days. The mixture was diluted with MeOH (50 mL) and Amberlyst A26 OH− (5 g) was added. The mixture was stirred for 1 h, filtered and the filtrate was concentrated to leave a viscous oil (539 mg). A 35-mg portion was purified by prep HPLC to afford the title compound (10.5 mg) as an oil. LC-MS Method 1 tR=1.02 min, m/z=359, 1H NMR (CDCl3) [selected resonances] 4.67 (s, 0.5H), 4.78 (s, 0.5H), 7.58 (d, 2H), 8.38 (d, 2H).

Workup

  1. additionwas added
  2. stirringThe mixture was stirred for 1 h
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-94c6ee748f9d47efb847e52b18a7bdfc
Source dataset
uspto-grants-2015_10
Patent number
US09163012B2

Reaction notes

Loading…