tert-butyl N-[(2S)-4-methyl-1-oxopentan-2-yl]carbamate → 4-t-Butyloxycarbonylamino-3-hydroxy-6-methylhept-1-ene

HRID 4259

反応式

HRID 4259 の反応式
[C:1]([NH:8][C@H:9]([CH:14]=[O:15])[CH2:10][CH:11]([CH3:13])[CH3:12])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH:16]([Mg]Br)=[CH2:17]>C1COCC1>[C:4]([O:3][C:1]([NH:8][CH:9]([CH2:10][CH:11]([CH3:12])[CH3:13])[CH:14]([OH:15])[CH:16]=[CH2:17])=[O:2])([CH3:6])([CH3:5])[CH3:7]

参加物

4

反応物 2

HCID 104275tert-butyl N-[(2S)-4-methyl-1-oxopentan-2-yl]carbamateHCID 178418507HCID 178418507、化合物

生成物 1

HCID 138560484-t-Butyloxycarbonylamino-3-hydroxy-6-methylhept-1-ene

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a stirred 0° C. solution of Boc-leucinal (3.00 g, 13.9 mmol) in dry THF (70 ml) was added vinyl magnesium bromide (35 ml of a 1.0M solution in THF). After 5 hours, the mixture was quenched with 1.0M NH4Cl (50 ml). Most of the THF was evaporated in vacuo and the residue was extracted with ether several times. The combined extracts were washed (brine), dried (Na2SO4), filtered, and evaporated to give the desired product as a 3:2 mixture of hydroxydiastereomers in 65% field.

後処理

  1. customthe mixture was quenched with 1.0M NH4Cl (50 ml)
  2. customMost of the THF was evaporated in vacuo
  3. extractionthe residue was extracted with ether several times
  4. washThe combined extracts were washed (brine)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated

出典と根拠

ORDレコード
ord-8bab05ee85f7428ab7f581565106fcda
出典データセット
uspto-grants-1988_02
特許番号
US04725584

関連ノート

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