Triphenylphosphine → (R)-4-(5-ethoxycarbonyl-3-phenoxymethyl-pyrazol-1-ylmethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

HRID 2046187Notes

Reaction equation

HRID 2046187 reaction equation
N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O.[CH2:17]([O:19][C:20]([C:22]1[NH:23][N:24]=[C:25]([CH2:27][O:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:26]=1)=[O:21])[CH3:18].[CH3:35][C:36]1([CH3:50])[O:40][CH2:39][C@@H:38]([CH2:41]O)[N:37]1[C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[C:46]([O:45][C:43]([N:37]1[C@H:38]([CH2:41][N:23]2[C:22]([C:20]([O:19][CH2:17][CH3:18])=[O:21])=[CH:26][C:25]([CH2:27][O:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[N:24]2)[CH2:39][O:40][C:36]1([CH3:35])[CH3:50])=[O:44])([CH3:49])([CH3:47])[CH3:48]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 11053464(R)-4-Hydroxymethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl esterHCID 178469067HCID 178469067, compound

Product 1

HCID 70654332(R)-4-(5-ethoxycarbonyl-3-phenoxymethyl-pyrazol-1-ylmethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl esterYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Di-tert-butyl azodicarboxylate (0.56 g, 2.43 mmol) was added portionwise to a mixture of 5-phenoxymethyl-2H-pyrazole-3-carboxylic acid ethyl ester (0.5 g, 2.0 mmol), (R)-1-boc-2,2-dimethyl-4-hydroxymethyl-oxazolidine (0.49 g, 2.1 mmol) and triphenylphosphine (0.64 g, 2.4 mmol) in THF (10 mL) at 0° C. The mixture was stirred at room temperature for 30 minutes. The solvent was evaporated in vacuo and the residue was purified by flash column chromatography (silica; DCM in heptane 50/50 to 100/0). Desired fractions were collected and the solvent evaporated in vacuo to yield (R)-4-(5-ethoxycarbonyl-3-phenoxymethyl-pyrazol-1-ylmethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (0.91 g, 98% yield) as a clear oil.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue was purified by flash column chromatography (silica; DCM in heptane 50/50 to 100/0)
  3. customDesired fractions were collected
  4. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-81becaf49c9b4daaba98c16ef9cfe871
Source dataset
uspto-grants-2013_11
Patent number
US08592422B2

Reaction notes

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