Triphenylphosphine → HCID 67530990, compound

HRID 2389090Notes

Reaction equation

HRID 2389090 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C@:12]1([CH3:18])[CH2:16][O:15][C:14](=[O:17])[NH:13]1)[CH:6]=[CH:5]2.[C@@H:19]12[CH2:25][C@@H:22]([CH2:23][CH2:24]1)[CH2:21][CH:20]2O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>>[C@@H:19]12[CH2:25][C@@H:22]([CH2:23][CH2:24]1)[CH2:21][CH:20]2[O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C@:12]1([CH3:18])[CH2:16][O:15][C:14](=[O:17])[NH:13]1)[CH:6]=[CH:5]2

Participants

5

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 10898676HCID 10898676, compoundHCID 51066623(R)-4-(6-hydroxynaphthalen-2-yl)-4-methyloxazolidin-2-one

Product 1

HCID 67530990HCID 67530990, compoundYield 40%

Procedure

The compound was prepared in a manner similar as to that described above (R)-4-(6-hydroxynaphthalen-2-yl)-4-methyloxazolidin-2-one, (1S,4R)-Bicyclo[2.2.1]heptan-2-ol (1.0 g, 0.0090 mol), triphenylphosphine (2.6 g, 0.0099 mol), h (45 mL, 0.55 mol), and diisopropyl azodicarboxylate (2.0 g, 0.0099 mol) to give 502 mg of the desired product as a white solid (40%). 1H NMR (400 MHz, CDCl3) δ=7.94-7.61 (m, 3 H), 7.50 (d, J=8.5 Hz, 1 H), 7.23-7.05 (m, 2 H), 4.67 (br. s., 2 H), 4.33-4.17 (m, 1 H), 3.84-3.51 (m, 2 H), 2.49-0.78 (m, 11H).

Workup

  1. customThe compound was prepared in a manner similar as to

Sources & evidence

ORD record
ord-7eca5be862054ec09f730dbf134f7766
Source dataset
uspto-grants-2012_09
Patent number
US08269043B2

Reaction notes

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