Triphenylphosphine → HCID 68690008, compound

HRID 1157801Notes

Reaction equation

HRID 1157801 reaction equation
[C:1]1([NH:7][C:8]([CH:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:56]([Si](C)(C)C)=[N+:57]=[N-:58]>O1CCCC1>[C:1]1([N:7]2[C:8]([CH:10]3[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]3)=[N:58][N:57]=[N:56]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 78378AzidotrimethylsilaneHCID 5363146Diisopropyl azodicarboxylateHCID 51204633HCID 51204633, compound

Product 1

HCID 68690008HCID 68690008, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Part B: To a solution of tert-butyl 4-(phenylcarbamoyl)piperidine-1-carboxylate (4.24 g, 13.9 mmol) and diisopropylazodicarboxylate (5.40 mL, 27.9 mmol) in tetrahydrofuran (100 mL) at 25° C. was added triphenylphosphine (7.31 g, 27.9 mmol). The resulting reaction mixture showed a slight exotherm, and the solution then was stirred at ambient temperature for ˜0.25 h until the reaction mixture had returned to 25° C. To the resulting mixture was added azidotrimethylsilane (3.65 mL, 27.9 mmol). A precipitate formed within minutes, and the mixture then was stirred at 25° C. for 7 days. The reaction mixture was concentrated under vacuum to afford the crude product. Column chromatography on silica gel (elution: 10-50% ethyl acetate/hexane) afforded tert-butyl 4-(1-phenyl-1H-tetrazol-5-yl)piperidine-1-carboxylate (2.58 g) as a white solid, following crystallization from a mixture of 1-chlorobutane/hexane; 1H NMR (300 MHz, CDCl3) δ 7.58 (m, 3H), 7.38 (m, 2H), 4.12 (m, 2H), 2.98 (m, 1H), 2.76 (m, 2H), 1.96-1.74 (m, 4H), 1.42 (s, 9H).

Workup

  1. customThe resulting reaction mixture
  2. customhad returned to 25° C
  3. customA precipitate formed within minutes
  4. stirringthe mixture then was stirred at 25° C. for 7 days
  5. concentrationThe reaction mixture was concentrated under vacuum
  6. customto afford the crude product

Sources & evidence

ORD record
ord-5b37ecb106c14b99b33fda305acab849
Source dataset
uspto-grants-2010_10
Patent number
US07807676B2

Reaction notes

Loading…