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

HRID 4256

Reaction equation

HRID 4256 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

HCID 13856049(3RS,4S)-4-(tert-butoxycarbonyl)amino-6-methylhepten-3-olYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-5281eca835b24f4999f7ce801feb6dce
Source dataset
uspto-grants-1988_02
Patent number
US04725583

Linked notes

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