tert-butyl N-[(2S)-4-methyl-1-oxopentan-2-yl]carbamate → (3RS,4S)-4-(tert-butoxycarbonyl)amino-6-methylhepten-3-ol

HRID 4256

반응식

HRID 4256 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]>O1CCCC1>[C:4]([O:3][C:1]([NH:8][C@@H: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 13856049(3RS,4S)-4-(tert-butoxycarbonyl)amino-6-methylhepten-3-ol수율 65%

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 tetrahydrofuran (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 hydroxy diastereomers in 65% yield.

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-5281eca835b24f4999f7ce801feb6dce
출처 데이터셋
uspto-grants-1988_02
특허 번호
US04725583

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