Ethylparaben → HCID 86587778、化合物

HRID 350331ノート

反応式

HRID 350331 の反応式
[C:1]([N:8]1[CH2:14][CH2:13][CH2:12][C@H:9]1[CH2:10][OH:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].O[C:16]1[CH:26]=[CH:25][C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:18][CH:17]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[C:4]([O:3][C:1]([N:8]1[CH2:14][CH2:13][CH2:12][C@H:9]1[CH2:10][O:11][C:16]1[CH:26]=[CH:25][C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:18][CH:17]=1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

参加物

6

反応物 4

HCID 8434EthylparabenHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 643448(S)-(-)-N-Boc-prolinol

生成物 1

HCID 86587778HCID 86587778、化合物収率 96.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

8,9 and 10 To a stirred mixture of Boc-prolinol (3.00 g, 14.9 mmol), ethyl p-hydroxybenzoate (2.40 g, 14.5 mmol), and triphenylphosphine (3.91 g, 14.9 mol) in THF (80 mL) was added dropwise diethyl azodicarboxylate (2.86 g, 16.4 mmol) at room temp. After the addition was completed, the resulting mixture was heated under reflux for 2 hr. After cooling, the mixture was concentrated in vacuo. The residue was dissolved in EtOAc and washed successively with 1 N NaOH, water, brine. The EtOAc layer was dried over MgSO4 and evaporated in vacuo. The residue was purified by column chromatography on silica gel with EtOAc-n-hexane (1:4, v/v) as eluent to give 4.88 g (93%) ethyl (S)-4-(1-tert-butoxycarbonyl-2-pyrrolidinyl)methoxybenzoate as an oil.

後処理

  1. additionAfter the addition
  2. temperaturethe resulting mixture was heated
  3. temperatureunder reflux for 2 hr
  4. temperatureAfter cooling
  5. concentrationthe mixture was concentrated in vacuo
  6. dissolutionThe residue was dissolved in EtOAc
  7. washwashed successively with 1 N NaOH, water, brine
  8. dry with materialThe EtOAc layer was dried over MgSO4
  9. customevaporated in vacuo
  10. customThe residue was purified by column chromatography on silica gel with EtOAc-n-hexane (1:4, v/v) as eluent

出典と根拠

ORDレコード
ord-9b3c320447a74c758c60581016bb5cdb
出典データセット
uspto-grants-2007_02
特許番号
US07179819B2

反応ノート

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