Tetrahydrofuran → (4R)-4-methyl-4-(6-(spiro[5.5]undecan-3-yloxy)-5-(trifluoromethyl)naphthalen-2-yl)oxazolidin-2-one

HRID 2389104Notes

Reaction equation

HRID 2389104 reaction equation
[CH2:1]1[C:6]2([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]2)[CH2:5][CH2:4][CH:3]([OH:12])[CH2:2]1.O[C:14]1[C:15]([C:31]([F:34])([F:33])[F:32])=[C:16]2[C:21](=[CH:22][CH:23]=1)[CH:20]=[C:19]([C@:24]1([CH3:30])[CH2:28][O:27][C:26](=[O:29])[NH:25]1)[CH:18]=[CH:17]2.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>C(Cl)Cl>[CH3:30][C@@:24]1([C:19]2[CH:18]=[CH:17][C:16]3[C:21](=[CH:22][CH:23]=[C:14]([O:12][CH:3]4[CH2:2][CH2:1][C:6]5([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]5)[CH2:5][CH2:4]4)[C:15]=3[C:31]([F:34])([F:32])[F:33])[CH:20]=2)[CH2:28][O:27][C:26](=[O:29])[NH:25]1

Participants

7

Reactant 5

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 46196301(R)-4-(6-hydroxy-5-(trifluoromethyl)naphthalen-2-yl)-4-methyloxazolidin-2-oneHCID 66926515Spiro[5.5]undecan-3-ol

Product 1

HCID 67413086(4R)-4-methyl-4-(6-(spiro[5.5]undecan-3-yloxy)-5-(trifluoromethyl)naphthalen-2-yl)oxazolidin-2-oneYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The mixture of spiro[5.5]undecan-3-ol (39.3 mg, 0.000234 mol) and (R)-4-(6-hydroxy-5-(trifluoromethyl)naphthalen-2-yl)-4-methyloxazolidin-2-one (60.6 mg, 0.000195 mol), and triphenylphosphine (61.2 mg, 0.000234 mol) in tetrahydrofuran (2 mL, 0.02 mol) was heated to reflux, and diisopropyl azodicarboxylate (0.0460 mL, 0.000234 mol) was added dropwise and was stirred and refluxed for overnight. The mixture was taken up into methylene chloride and subjected to chromatography purification with EtOAc/hexane (10:90 to 80:20) to give (4R)-4-methyl-4-(6-(spiro[5.5]undecan-3-yloxy)-5-(trifluoromethyl)naphthalen-2-yl)oxazolidin-2-one as a white solid (62.5 mg, 70%). LCMS Rf=2.45 min 462.40 ([M+1]+, 70%), 503.43 [M+42], 100%).

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. temperaturerefluxed for overnight
  4. customsubjected to chromatography purification with EtOAc/hexane (10:90 to 80:20)

Sources & evidence

ORD record
ord-b9eb7dc74d8b439bb92e58ae9dad37a6
Source dataset
uspto-grants-2012_09
Patent number
US08269043B2

Reaction notes

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