Phenol → HCID 16106960, compound

HRID 1911512Notes

Reaction equation

HRID 1911512 reaction equation
[OH:1][CH2:2][C@@H:3]1[CH2:7][O:6][C:5]([CH3:9])([CH3:8])[N:4]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].[C:17]1(O)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>C1COCC1>[C:13]([O:12][C:10]([N:4]1[C@H:3]([CH2:2][O:1][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:7][O:6][C:5]1([CH3:8])[CH3:9])=[O:11])([CH3:16])([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 996PhenolHCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 11053464(R)-4-Hydroxymethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Product 1

HCID 16106960HCID 16106960, compoundYield 63.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of tert-butyl (R)-4-(hydroxymethyl)-2,2-dimethyl-3-oxazolidinecarboxylate (400 mg; CAS 108149-63-9) in THF (20 ml) were added phenol (197 mg), triphenylphosphine (573 mg) and di-tert-butyl azodicarboxylate (488 mg). The resulting yellow solution was stirred at 70° C. for 18 h overnight, then concentrated in vacuo. The crude product was purified by column chromatography (SiO2; gradient: heptane/EtOAc 100:0->70:30) to give (R)-2,2-dimethyl-4-phenoxymethyl-oxazolidine-3-carboxylic acid tert-butyl ester (336 mg, 63%) as a colourless viscous oil. MS (ISP): 308.3 ([M+H]+)).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe crude product was purified by column chromatography (SiO2; gradient: heptane/EtOAc 100:0->70:30)

Sources & evidence

ORD record
ord-cb267195a7484643912f635120f360e7
Source dataset
uspto-grants-2013_12
Patent number
US08604061B2

Reaction notes

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