Cyclohexanol → HCID 67411654, compound

HRID 2389082Notes

Reaction equation

HRID 2389082 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(O)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.[C:26]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:31]=CC=C[CH:27]=1.O1CCCC1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>>[CH:26]([CH:19]1[CH2:24][CH2:23][CH:22]([O:1][C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[CH:8]=[C:7]([C@:12]2([CH3:18])[CH2:16][O:15][C:14](=[O:17])[NH:13]2)[CH:6]=[CH:5]3)[CH2:21][CH2:20]1)([CH3:31])[CH3:27]

Participants

6

Reactant 5

HCID 7966CyclohexanolHCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 51066623(R)-4-(6-hydroxynaphthalen-2-yl)-4-methyloxazolidin-2-one

Product 1

HCID 67411654HCID 67411654, compoundYield 52%

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 (2.0 g, 0.0082 mol), cyclohexanol, 4-(1-methylethyl)-(1.3 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 1.6 g of the desired product as a yellow solid (52%). ESI-MS: 368 (M+H)+. 1H NMR (400 MHz, CDCl3) δ=7.81-7.59 (m, 2 H), 7.49-7.30 (m, 1 H), 7.22-7.04 (m, 2 H), 6.88-6.64 (m, 1 H), 4.66 (br. s., 1 H), 4.40 (s, 2 H), 4.34-4.18 (m, 1 H), 2.29-2.07 (m, 2 H), 1.91-1.69 (m, 6 H), 1.64-1.09 (m, 5 H), 0.96-0.69 (m, 6 H).

Workup

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

Sources & evidence

ORD record
ord-3d4adf1b21de49f9b5339891f4514b15
Source dataset
uspto-grants-2012_09
Patent number
US08269043B2

Reaction notes

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