Tetrahydrofuran → HCID 67413948, compound

HRID 2389084Notes

Reaction equation

HRID 2389084 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.[CH:19]1([CH:24]2[CH2:29][CH2:28][CH:27](O)[CH2:26][CH2:25]2)[CH2:23][CH2:22][CH2:21][CH2:20]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O1CCCC1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>>[CH:19]1([CH:24]2[CH2:25][CH2:26][CH:27]([O:1][C:2]3[CH:3]=[C:4]4[C:9](=[CH:10][CH:11]=3)[CH:8]=[C:7]([C@:12]3([CH3:18])[CH2:16][O:15][C:14](=[O:17])[NH:13]3)[CH:6]=[CH:5]4)[CH2:28][CH2:29]2)[CH2:20][CH2:21][CH2:22][CH2:23]1

Participants

6

Reactant 5

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 15767265HCID 15767265, compoundHCID 51066623(R)-4-(6-hydroxynaphthalen-2-yl)-4-methyloxazolidin-2-one

Product 1

HCID 67413948HCID 67413948, compoundYield 27%

Procedure

The compound was prepared in a manner similar as to that described above using (R)-4-(6-hydroxynaphthalen-2-yl)-4-methyloxazolidin-2-one, 4-cyclopentyl-cyclohexanol (1.5 g, 0.0090 mol), triphenylphosphine (2.6 g, 0.0099 mol), tetrahydrofuran (45 mL, 0.55 mol) and diisopropyl azodicarboxylate (2.0 g, 0.0099 mol) to give 895 mg of a 1.6 to 1 diasteromeric ratio of the desired compound as a yellow solid (27%). ESI-MS: 368 (M+H)+. 1H NMR (400 MHz, CDCl3) δ=7.80-7.63 (m, 3 H), 7.39 (dd, J=1.9, 8.7 Hz, 1 H), 7.22-7.08 (m, 2 H), 4.70-4.58 (br. s., 0.63 H), 4.43-4.36 (s, 2 H), 4.34-4.21 (tt, J=4.2, 6.5 Hz, 0.39 H), 2.04 (s, 2 H), 1.87-1.70 (m, 2 H), 1.65-0.77 (m, 17 H)

Workup

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

Sources & evidence

ORD record
ord-78dc969e3d3f47b68768c18ea418d281
Source dataset
uspto-grants-2012_09
Patent number
US08269043B2

Reaction notes

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