Triphenylphosphine → HCID 67972218, compound

HRID 1804603Notes

Reaction equation

HRID 1804603 reaction equation
[CH:1]1([NH:4][C:5]([CH:7]2[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]2)=O)[CH2:3][CH2:2]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.C[Si]([N:57]=[N+:58]=[N-:59])(C)C>C1COCC1>[CH:1]1([N:4]2[C:5]([CH:7]3[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]3)=[N:59][N:58]=[N:57]2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 78378AzidotrimethylsilaneHCID 5363146Diisopropyl azodicarboxylateHCID 24688815tert-Butyl 4-(cyclopropylcarbamoyl)piperidine-1-carboxylate

Product 1

HCID 67972218HCID 67972218, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound from Step A above (200 mg, 0.745 mmol) and triphenylphosphine (391 mg, 1.49 mmol) were placed in a 50 ml round bottom flask and then THF (20 ml) was added followed by DIAD (0.29 mL, 1.49 mol) at RT. After 5 min of stirring, trimethylsilylazide (0.2 mL, 1.50 mmol) was added and the resulting mixture was stirred overnight at RT. The volatiles were removed under reduced pressure and the resulting residue was partitioned between ethyl acetate and brine, combined, dried over sodium sulfate, filtered and concentrated. The material was purified by Mass Directed HPLC to give the title compound (52 mg, 24%) as a clear oil/film. ESI-MS calculated for C14H23N5O2: Exact Mass: 293.38. Found 194.35 (M-Boc)+ and 316.36 (MNa)+.

Workup

  1. stirringthe resulting mixture was stirred overnight at RT
  2. customThe volatiles were removed under reduced pressure
  3. customthe resulting residue was partitioned between ethyl acetate and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe material was purified by Mass Directed HPLC

Sources & evidence

ORD record
ord-03b96f79754d4007895cbd90867d73c7
Source dataset
uspto-grants-2013_01
Patent number
US08354403B2

Reaction notes

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