Water → HCID 59406928, compound

HRID 1948367Notes

Reaction equation

HRID 1948367 reaction equation
[N:1]([CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:6][CH:5]1[O:15][CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[N+]=[N-].O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1>[NH2:1][CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:6][CH:5]1[O:15][CH2:16][C:17]([O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:18]

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 86643344HCID 86643344, compound2×

Product 1

HCID 59406928HCID 59406928, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 4-azido-3-(2-tert-butoxy-2-oxoethoxy)piperidine-1-carboxylate (Intermediate 239, 1.75 g) was dissolved in THF (60 mL), followed by the addition of deionised water (5 mL) and PS-triphenylphosphine resin (10.6 g), and stirred at room temperature over the week-end. The reaction mixture was filtered, and the resin was rinsed repeatedly with MeOH and a 1:5 MeOH:DCM mixture, and the filtrate was concentrated in vacuo, yielding the title compound (1.20 g, 75%). MS (GC-EI)[(M)+]: 302 for C14H26N2O5.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe resin was rinsed repeatedly with MeOH
  3. concentrationa 1:5 MeOH:DCM mixture, and the filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-737a7454d065486bad87fe34a05be0a9
Source dataset
uspto-grants-2013_03
Patent number
US08399489B2

Reaction notes

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