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

HRID 4259

반응식

HRID 4259 반응식
[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]

참가 물질

4

반응물 2

HCID 104275tert-butyl N-[(2S)-4-methyl-1-oxopentan-2-yl]carbamateHCID 178418507HCID 178418507, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8bab05ee85f7428ab7f581565106fcda
출처 데이터셋
uspto-grants-1988_02
특허 번호
US04725584

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