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

HRID 4259

Reaction equation

HRID 4259 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]>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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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.

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-8bab05ee85f7428ab7f581565106fcda
Source dataset
uspto-grants-1988_02
Patent number
US04725584

Linked notes

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