Tetrahydrofuran → (R)-4-(6-(4,4-dimethylcyclohexyloxy)naphthalen-2-yl)-4-methyloxazolidin-2-one

HRID 1036409

反応式

HRID 1036409 の反応式
[CH3:1][C:2]1([CH3:9])[CH2:7][CH2:6][CH:5]([OH:8])[CH2:4][CH2:3]1.O[C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[CH:17]=[C:16]([C@:21]1([CH3:27])[CH2:25][O:24][C:23](=[O:26])[NH:22]1)[CH:15]=[CH:14]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>CC(=O)OCC>[CH3:1][C:2]1([CH3:9])[CH2:7][CH2:6][CH:5]([O:8][C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[CH:17]=[C:16]([C@:21]2([CH3:27])[CH2:25][O:24][C:23](=[O:26])[NH:22]2)[CH:15]=[CH:14]3)[CH2:4][CH2:3]1

参加物

7

反応物 5

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 136735Cyclohexanol, 4,4-dimethyl-HCID 51066623(R)-4-(6-hydroxynaphthalen-2-yl)-4-methyloxazolidin-2-one

生成物 1

HCID 67414756(R)-4-(6-(4,4-dimethylcyclohexyloxy)naphthalen-2-yl)-4-methyloxazolidin-2-one

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

To a mixture of 4,4-Dimethylcyclohexanol (63.2 mg, 0.000493 mol), (R)-4-(6-hydroxynaphthalen-2-yl)-4-methyl-oxazolidin-2-one (100 mg, 0.0004 mol), triphenylphosphine (129 mg, 0.000493 mol), and tetrahydrofuran (4 mL, 0.05 mol), diisopropyl azodicarboxylate (0.0971 mL, 0.000493 mol) was added dropwise and was stirred at room temperature overnight. The mixture was diluted with EA and washed with 5% citric acid and brine then dried with magnesium sulfate and concentrated. The crude was taken up into DCM and subjected to ISCO combiflash purification with EtOAc/hexane (0-70) to give product.

後処理

  1. additionwas added dropwise
  2. washwashed with 5% citric acid and brine
  3. dry with materialthen dried with magnesium sulfate
  4. concentrationconcentrated
  5. customsubjected to ISCO combiflash purification with EtOAc/hexane (0-70)
  6. customto give product

出典と根拠

ORDレコード
ord-f596cea7211341bfb4f59d8cbd5f546d
出典データセット
uspto-grants-2013_10
特許番号
US08546359B2

関連ノート

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