Diisopropylcarbodiimide → HCID 59178969, compound

HRID 2093473Notes

Reaction equation

HRID 2093473 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][CH:16]([CH:19]3[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]3)[CH2:15][CH2:14]2)=[CH:9][CH:8]=1)=O.C(N=C=NC(C)C)(C)C>O1CCOCC1.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.[Cu+2]>[C:28]([O:27][C:25]([N:22]1[CH2:23][CH2:24][CH:19]([CH:16]2[CH2:15][CH2:14][N:13]([C:10]3[CH:9]=[CH:8][C:7]([C:5]4[O:1][CH2:2][CH2:3][N:4]=4)=[CH:12][CH:11]=3)[CH2:18][CH2:17]2)[CH2:20][CH2:21]1)=[O:26])([CH3:29])([CH3:31])[CH3:30]

Participants

5

Reactant 2

HCID 12734DiisopropylcarbodiimideHCID 59178987HCID 59178987, compound

Product 1

HCID 59178969HCID 59178969, compound

Reagents, catalysts & solvents 2

HCID 2734996copper(II) trifluoromethanesulfonateCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl 1′-(4-{[(2-hydroxyethyl)amino]carbonyl}phenyl)-4,4′-bipiperidine-1-carboxylate (234 mg; 0.542 mmol) in dioxane (5 mL) was treated with N,N′-diisopropylcarbodiimide (68 mg; 0.084 mmol) and Cu(OTf)2 (10 mg; 0.027 mmol). The mixture was refluxed for 5 hr. The reaction was evaporated and chromatographed (PTLC; 40:1 CH2Cl2/MeOH), giving the title compound.

Workup

  1. temperatureThe mixture was refluxed for 5 hr
  2. customThe reaction was evaporated
  3. customchromatographed (PTLC; 40:1 CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-081edca949c24b828542bae0638533d3
Source dataset
uspto-grants-2013_05
Patent number
US08445499B2

Reaction notes

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