Triphenylphosphine → HCID 21906208, compound

HRID 1247074Notes

Reaction equation

HRID 1247074 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:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][CH:28]([CH2:31]O)[CH2:27][CH2:26]1)=[O:24])([CH3:21])([CH3:20])[CH3:19].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N+](C(OCC)=O)(C(OCC)=O)=[N-]>C1COCC1>[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][CH2:31][CH:28]2[CH2:29][CH2:30][N:25]([C:23]([O:22][C:18]([CH3:19])([CH3:21])[CH3:20])=[O:24])[CH2:26][CH2:27]2)=[N:6][CH:7]=1

Participants

6

Reactant 4

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

Product 1

HCID 21906208HCID 21906208, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of N-(5-chloropyridin-2-yl)-2-hydroxybenzamide (200 mg, 0.806 mmol), 1-tert-butoxycarbonylpiperidine-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-56f635a5b45940d7886cf0a032eb8baa
Source dataset
uspto-grants-2006_10
Patent number
US07129245B2

Reaction notes

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