Triphenylphosphine → Benzyl 4-[1-(4-chloro-3-methylphenyl)-1H-tetrazol-5-yl]piperidine-1-carboxylate

HRID 1045804Notes

Reaction equation

HRID 1045804 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([CH:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:18])[CH2:13][CH2:12]2)=O)=[CH:4][C:3]=1[CH3:27].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:65]=[N+:66]=[N-:67])(C)C>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:9]([CH:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[O:18])[CH2:13][CH2:12]3)=[N:67][N:66]=[N:65]2)=[CH:4][C:3]=1[CH3:27]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 78378AzidotrimethylsilaneHCID 5363146Diisopropyl azodicarboxylateHCID 86685835Benzyl 4-[(4-chloro-3-methyl-phenyl)carbamoyl]piperidine-1-carboxylate

Product 1

HCID 86685836Benzyl 4-[1-(4-chloro-3-methylphenyl)-1H-tetrazol-5-yl]piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product from step A (840 mg, 2.171 mmol) and triphenylphosphine (1139 mg, 4.34 mmol) in THF (8.0 ml) was treated with diisopropylazodicarboxylate (0.844 ml, 4.34 mmol) and trimethylsilyl azide (0.574 ml, 4.34 mmol) at rt. The mixture was stirred at rt for 24 h, then quenched with aqueous saturated NaHCO3, and extracted with MTBE. The combined organic layers were concentrated. Purification of the resulting crude product on SiO2 (0 to 100% EtOAc, hexanes) afforded the title compound as a clear colorless oil. HPLC/MS: 412.2/414.1 (M+1); Rt=1.22 min (LC2).

Workup

  1. customquenched with aqueous saturated NaHCO3
  2. extractionextracted with MTBE
  3. concentrationThe combined organic layers were concentrated
  4. customPurification of the resulting crude product on SiO2 (0 to 100% EtOAc, hexanes)

Sources & evidence

ORD record
ord-2d8c3e79343c4082867961a545480751
Source dataset
uspto-grants-2013_10
Patent number
US08569299B2

Reaction notes

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