Tetrahydrofuran → HCID 18539256, compound

HRID 1726139Notes

Reaction equation

HRID 1726139 reaction equation
C[Si](C)(C)[C:3]1[S:4][CH:5]=[CH:6][N:7]=1.[C:10]([O:14][C:15](C1CCC(C=O)CC1)=[O:16])([CH3:13])([CH3:12])[CH3:11].CC[CH2:27][CH2:28][N+:29](CCCC)(CCCC)CCCC.[F-].[CH2:43]1[CH2:47][O:46][CH2:45][CH2:44]1>>[C:10]([O:14][C:15]([N:29]1[CH2:45][CH2:44][CH:43]([CH:47]([OH:46])[C:3]2[S:4][CH:5]=[CH:6][N:7]=2)[CH2:27][CH2:28]1)=[O:16])([CH3:11])([CH3:12])[CH3:13]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 5884532-TrimethylsilylthiazoleHCID 2724141Tetrabutylammonium FluorideHCID 866021302782759-60-6

Product 1

HCID 18539256HCID 18539256, compoundYield 50%

Procedure

2-(Trimethylsilyl)thiazole (1.0 g, 6.36 mmol) and 4-formyl-cyclohexanecarboxylic acid tert-butyl ester (1.63 g, 7.63 mmol) were stirred at room temperature for 4 hours. THF (50 mL) and TBAF (1M in THF, 7.6 mL, 7.6 mmol) were added and the mixture stirred for an additional hour. Standard work-up and purification afforded 4-(hydroxy-thiazol-2-yl-methyl)-piperidine-1-carboxylic acid tert-butyl ester as a beige syrup (940 mg, 50%).

Workup

  1. customStandard work-up and purification

Sources & evidence

ORD record
ord-7945b73da7164885b1f529f83f10f237
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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