Triphenylphosphine → 3-{2-[1-(4-Isoquinolyl)-4-piperidyl]ethyl)-1,3-oxazolidine-2,4-dione

HRID 1663037Notes

Reaction equation

HRID 1663037 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([N:11]2[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18]O)[CH2:13][CH2:12]2)=[CH:3][N:2]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[O:39]1[CH2:43][C:42](=[O:44])[NH:41][C:40]1=[O:45].N(C(OC(C)C)=O)=NC(OC(C)C)=O>>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([N:11]2[CH2:12][CH2:13][CH:14]([CH2:17][CH2:18][N:41]3[C:42](=[O:44])[CH2:43][O:39][C:40]3=[O:45])[CH2:15][CH2:16]2)=[CH:3][N:2]=1

Participants

5

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 973892,4-OxazolidinedioneHCID 210969212-[1-(4-Isoquinolyl)-4-piperidyl]ethanol

Product 1

HCID 210969623-{2-[1-(4-Isoquinolyl)-4-piperidyl]ethyl)-1,3-oxazolidine-2,4-dioneYield 94.4%

Procedure

The procedure described in Example 5 (step 5.2) is used. Starting with 0.801 g (3.12 mmol) of 2-[1-(4-isoquinolyl)-4-piperidyl]ethanol, prepared in step 7.1, 0.902 g (3.44 mmol) of triphenylphosphine, 0.379 g (3.75 mmol) of 1,3-oxazolidine-2,4-dione and 0.632 g (3.12 mmol) of diisopropyl azodicarboxylate (DIAD), and after chromatography on silica gel, eluting with a 98/2 mixture of dichloromethane and methanol, 1 g of product is obtained in the form of a green paste.

Workup

  1. washafter chromatography on silica gel, eluting with a 98/2 mixture of dichloromethane and methanol

Sources & evidence

ORD record
ord-5ed5f7598fb44e3396d95c03abf0f303
Source dataset
uspto-grants-2011_10
Patent number
US08034818B2

Reaction notes

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