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Sodium hydride → N-Boc-O-(2,2,5,5-tetramethyl-1-cyclopentyl)-1-amino-1-hydroxymethylcyclopropane

HRID 1731685
ノート
印刷プレビュー

反応式

HRID 1731685 の反応式
[CH3:1][C:2]1([CH3:10])[CH2:6][CH2:5][C:4]([CH3:8])([CH3:7])[CH:3]1[OH:9].[H-].[Na+].C1OCCOCCOCCOCCOCCOC1.CCOCC.S(O)(=O)(=O)C.[C:41]([NH:48][C:49]1([CH2:52]O)[CH2:51][CH2:50]1)([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42]>C(#N)C.O1CCCC1>[C:41]([NH:48][C:49]1([CH2:52][O:9][CH:3]2[C:4]([CH3:8])([CH3:7])[CH2:5][CH2:6][C:2]2([CH3:10])[CH3:1])[CH2:51][CH2:50]1)([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 24758Sodium hydrideHCID 5516962,2,5,5-Tetramethylcyclopentan-1-olHCID 20092326Ethoxyethane;1,4,7,10,13,16-hexaoxacyclooctadecaneHCID 20165745N-Boc-1-amino-1-hydroxymethylcyclopropane mesylate

生成物 1

HCID 20165730N-Boc-O-(2,2,5,5-tetramethyl-1-cyclopentyl)-1-amino-1-hydroxymethylcyclopropane

試薬・触媒・溶媒 2

HCID 6342
Acetonitrile
溶媒
HCID 8028Tetrahydrofuran溶媒2 回

実験手順

2,2,5,5-Tetramethyl-1-cyclopentanol is added to a dry flask under argon at 0° C. Dry tetrahydrofuran is added with a syringe. Sodium hydride (60% dispersion in oil) is added quickly in one portion and the contents of the flask are stirred for one hour at room temperature. A 10 mM solution of 18-crown-6- ether in acetonitrile is added with a syringe and the flask cooled to 0° C. A tetrahydrofuran solution of N-Boc-1-amino-1-hydroxymethylcyclopropane mesylate is added with vigorous stirring over a 10 minute period. After completion of the reaction, as judged by thin layer chromatography, it is quenched with dimethyl sulfate, poured into saturated ammonium chloride and extracted with ethyl acetate. The organic layer is dried over MgSO4 and evaporated to yield N-Boc-O-(2,2,5,5-tetramethyl-1-cyclopentyl)-1-amino-1-hydroxymethylcyclopropane.

後処理

  1. temperaturethe flask cooled to 0° C
  2. stirringwith vigorous stirring over a 10 minute period
  3. customAfter completion of the reaction
  4. customis quenched with dimethyl sulfate
  5. additionpoured into saturated ammonium chloride
  6. extractionextracted with ethyl acetate
  7. dry with materialThe organic layer is dried over MgSO4
  8. customevaporated

出典と根拠

ORDレコード
ord-fc2ab26bae4748f5ac9058042d4d93d0
出典データセット
uspto-grants-1986_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04622418

反応ノート

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