Benzyl Alcohol → {2-hydroxy-1-[3-(tetrahydropyran-2-yloxy)octyl]-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalen-5-yloxy}acetic acid benzyl ester

HRID 1053550

反応式

HRID 1053550 の反応式
[OH:1][CH:2]1[CH:19]([CH2:20][CH2:21][CH:22]([O:28][CH:29]2[CH2:34][CH2:33][CH2:32][CH2:31][O:30]2)[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH:5]2[CH2:6][C:7]3[C:12]([CH2:13][CH:4]2[CH2:3]1)=[C:11]([O:14][CH2:15][C:16]([OH:18])=[O:17])[CH:10]=[CH:9][CH:8]=3.[CH2:35](O)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.C(N(CC)CC)C.O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1>ClCCl.COC(C)(C)C>[CH2:35]([O:17][C:16](=[O:18])[CH2:15][O:14][C:11]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:12]=1[CH2:13][CH:4]1[CH2:3][CH:2]([OH:1])[CH:19]([CH2:20][CH2:21][CH:22]([O:28][CH:29]3[CH2:34][CH2:33][CH2:32][CH2:31][O:30]3)[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH:5]1[CH2:6]2)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

参加物

7

反応物 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 90281645{2-hydroxy-1-[3-(tetrahydropyran-2-yloxy)octyl]-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalen-5-yloxy}acetic acid2 回

生成物 1

HCID 121480749{2-hydroxy-1-[3-(tetrahydropyran-2-yloxy)octyl]-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalen-5-yloxy}acetic acid benzyl ester

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 15413tert-Butyl methyl ether溶媒

実験手順

A solution of {2-hydroxy-1-[3-(tetrahydropyran-2-yloxy)octyl]-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalen-5-yloxy}acetic acid (Compound B) (2 g, 4.21 mmol), benzyl alcohol (2.47 g, 22.9 mmol) and triethylamine (7.2 g, 71.3 mmol) in dichloromethane (DCM) (20 mL) was treated with bis(2-oxo-3-oxazolidinyl)phosphinic chloride (BOP—Cl) (7.8 g, 30.7 mmol) at 0° C. and stirred at room temperature (RT) for 2 hr. The reaction mixture was diluted with methyl-tert-butyl ether (MTBE) and washed with water and then brine, dried over sodium sulfate and concentrated under vacuum. The residue was purified by silica gel chromatography to provide Compound C. MS: m/z 587 [M+Na]+

後処理

  1. washwashed with water
  2. dry with materialbrine, dried over sodium sulfate
  3. concentrationconcentrated under vacuum
  4. customThe residue was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-c97958e20147431792fafb6122448452
出典データセット
uspto-grants-2016_07
特許番号
US09394227B1

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