Triphenylphosphine → 4-[4-Methyl-5-(4-tetrazol-1-yl-phenoxymethyl)-thiazol-2-yl]-piperidine-1-carboxylic acid tert-butyl ester

HRID 871934Notes

Reaction equation

HRID 871934 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[S:15][C:16]([CH2:20][OH:21])=[C:17]([CH3:19])[N:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N:22]1([C:27]2[CH:32]=[CH:31][C:30](O)=[CH:29][CH:28]=2)[CH:26]=[N:25][N:24]=[N:23]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[S:15][C:16]([CH2:20][O:21][C:30]3[CH:31]=[CH:32][C:27]([N:22]4[CH:26]=[N:25][N:24]=[N:23]4)=[CH:28][CH:29]=3)=[C:17]([CH3:19])[N:18]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 5429104-(1H-1,2,3,4-tetrazol-1-yl)phenolHCID 7164575tert-Butyl 4-[5-(hydroxymethyl)-4-methyl-1,3-thiazol-2-yl]tetrahydro-1(2H)-pyridinecarboxylate

Product 1

HCID 579868274-[4-Methyl-5-(4-tetrazol-1-yl-phenoxymethyl)-thiazol-2-yl]-piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(5-Hydroxymethyl-4-methyl-thiazol-2-yl)-piperidine-1-carboxylic acid tert-butyl ester (1.00 g, 3.2 mmol) in THF (6.4 mL) was added, 4-tetrazol-1-yl-phenol (0.52 g, 3.2 mmol), polymer bound triphenylphosphine (3 mmol/g, 1.6 g). To this solution was added ditertierybutylazodicarboxylate (1.1 g, 4.8 mmol), stirred for 4 hours and filtered through a pad of celite. The filtrate was concentrated and purified by silica gel chromatography to provide the desired product. 1H NMR (CDCl3): δ 9.01 (1H, s), 7.66 (2H, d), 7.15 (2H, d), 5.21 (2H, s), 4.19 (2H, m), 3.10 (1H, m), 2.86 (2H, m), 2.45 (3H, s), 2.08 (2H, m), 1.72 (2H, m), 1.47 (9H, s).

Workup

  1. additionTo this solution was added ditertierybutylazodicarboxylate (1.1 g, 4.8 mmol)
  2. filtrationfiltered through a pad of celite
  3. concentrationThe filtrate was concentrated
  4. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-de653f933b3e4b92a06620182fa8c581
Source dataset
uspto-grants-2015_03
Patent number
US08975258B2

Reaction notes

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