Diisopropylcarbodiimide → HCID 59178969, compound

HRID 1947674Notes

Reaction equation

HRID 1947674 reaction equation
ClC1N=CN=C([N:8]2[CH2:13][CH2:12][CH:11]([CH:14]3[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]3)[CH2:10][CH2:9]2)C=1.O[CH2:28][CH2:29][NH:30][C:31]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1C1(C2CCNCC2)CCN(C([O-])=O)CC1)=[O:32].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:23]([O:22][C:20]([N:17]1[CH2:18][CH2:19][CH:14]([CH:11]2[CH2:12][CH2:13][N:8]([C:36]3[CH:37]=[CH:38][C:33]([C:31]4[O:32][CH2:28][CH2:29][N:30]=4)=[CH:34][CH:35]=3)[CH2:9][CH2:10]2)[CH2:15][CH2:16]1)=[O:21])([CH3:26])([CH3:25])[CH3:24]

Participants

6

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 59178818HCID 59178818, compoundHCID 131730302HCID 131730302, 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-6b8f482ff5304057a7a6ca0e8a766c9e
Source dataset
uspto-grants-2013_03
Patent number
US08399485B2

Reaction notes

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