Tetrahydrofuran → HCID 9802430, compound

HRID 1882974Notes

Reaction equation

HRID 1882974 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:17])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[OH:16])=[N:6][CH:7]=1.C(OC([N:25]1[CH2:30][CH2:29]C(CO)[CH2:27][CH2:26]1)=O)(C)(C)C.[C:33]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N+](C(OCC)=O)(C(OCC)=O)=[N-].[CH2:64]1[CH2:68]O[CH2:66][CH2:65]1>>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:17])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH2:66][CH:65]2[CH2:29][CH2:30][N:25]([CH:26]([CH3:27])[CH3:33])[CH2:68][CH2:64]2)=[N:6][CH:7]=1

Participants

6

Reactant 5

HCID 8028Tetrahydrofuran2×HCID 11776Triphenylphosphine2×HCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylateHCID 8033597N-(5-chloropyridin-2-yl)-2-hydroxybenzamideHCID 14357405Diethyldiazodicarboxylate2×

Product 1

HCID 9802430HCID 9802430, compoundYield 40%

Procedure

A solution of N-(5-chloropyridin-2-yl)-2-hydroxy-benzamide (200 mg, 0.806 mmol), 1-tert-butoxycarbonyl-piperidine-4-methanol (191 mg, 0.887 mmol), and triphenylphosphine (232 mg, 0.887 mmol) in THF was treated dropwise with a THF solution of diethyl diazodicarboxylate (DEAD) (0.14 mL, 0.887 mmol in 1 mL of THF). After 16 h, the mixture was treated with an additional equivalent of triphenylphosphine and DEAD. After 2 h, the mixture was concentrated, diluted with methylene chloride, and filtered. The solid collected was the desired product (128 mg, 36%). The filtrate was purified by column chromatography (SiO2; 4:1 hexanes:EtOAc) providing an additional 142 mg (40%) of the title compound.

Workup

  1. waitAfter 2 h
  2. concentrationthe mixture was concentrated
  3. additiondiluted with methylene chloride
  4. filtrationfiltered
  5. customThe solid collected
  6. customThe filtrate was purified by column chromatography (SiO2; 4:1 hexanes:EtOAc)

Sources & evidence

ORD record
ord-e6eddfa9bfda489dad97ebff4bb21d96
Source dataset
uspto-grants-2004_07
Patent number
US06759414B2

Reaction notes

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