Tetrahydrofuran → tert-Butyl hydrogen (1,5-dihydroxypentan-2-yl)carbonimidate

HRID 1257571ノート

反応式

HRID 1257571 の反応式
C1COCC1.[Li+].[BH4-].[C:8]([O:12][C:13]([NH:15][C@@H:16]([CH2:21][CH2:22][C:23](OC)=[O:24])[C:17](OC)=[O:18])=[O:14])([CH3:11])([CH3:10])[CH3:9]>CO>[OH:18][CH2:17][C@@H:16]([NH:15][C:13](=[O:14])[O:12][C:8]([CH3:10])([CH3:9])[CH3:11])[CH2:21][CH2:22][CH2:23][OH:24]

参加物

5

反応物 3

HCID 8028Tetrahydrofuran2 回HCID 2734644Dimethyl N-(tert-Butoxycarbonyl)-L-glutamateHCID 4148881Lithium borohydride

生成物 1

HCID 2734851tert-Butyl hydrogen (1,5-dihydroxypentan-2-yl)carbonimidate収率 91.7%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

A 20 L reactor was charged with 10 L of dry THF and LiBH4 (400 g) and cooled to 0° C. A THF solution of (S)-dimethyl 2-(tert-butoxycarbonylamino)pentanedioate (1000 g/3.63 mol, dissolved in 2 L of dry THF) was then added dropwise while keeping the internal temp. below 15° C. The mixture was slowly warmed to room temperature and stirred for 16 h. Cooled to 0° C., then MeOH (10 L) was added dropwise to the reaction mixture to quench the excess amount of reducing reagent. Concentrated, and the residue was poured into 5 L water. After extraction with ethyl acetate, the combined organic phase was dried over Na2SO4. After filtration the solvent was removed in vacuo to give 730 g of crude (S)-tert-butyl 1,5-dihydroxypentan-2-ylcarbamate as a pale yellow oil.

後処理

  1. custombelow 15° C
  2. temperatureThe mixture was slowly warmed to room temperature
  3. temperatureCooled to 0° C.
  4. customto quench the excess amount of reducing reagent
  5. concentrationConcentrated
  6. additionthe residue was poured into 5 L water
  7. extractionAfter extraction with ethyl acetate
  8. dry with materialthe combined organic phase was dried over Na2SO4
  9. filtrationAfter filtration the solvent
  10. customwas removed in vacuo

出典と根拠

ORDレコード
ord-e34b1d13c47d4946a7b4176add2ab383
出典データセット
uspto-grants-2013_06
特許番号
US08461328B2

反応ノート

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