Isobutyraldehyde → HCID 57687748, compound

HRID 1880816Notes

Reaction equation

HRID 1880816 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][C@H:12]([NH2:15])[CH2:13][OH:14])([CH3:4])([CH3:3])[CH3:2].[CH:17](=O)[CH:18]([CH3:20])[CH3:19].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:16])[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][C@H:12]([NH:15][CH2:17][CH:18]([CH3:20])[CH3:19])[CH2:13][OH:14])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6561IsobutyraldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 57687745359867-97-3

Product 1

HCID 57687748HCID 57687748, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-(5-Amino-6-hydroxy-hexyl)-carbamic acid tert-butyl ester (3) (6.85 g) was dissolved in 200 mL CH2Cl2. Isobutyraldehyde (2.67 mL) was added and this solution was stirred for 2 hours. Sodium triacetoxyborohydride (1.1 eq) was added and the solution was stirred for 2 hours at RT. The solution was washed with sat. NaHCO3. The milky organic phase was separated and evaporated to dryness. The residue was purified by column chromatography using 99:1 EtOAc (100%) to EtOAc-MeOH(NH3) 99-1. as the eluent. Fractions containing the product were evaporated yielding 2.60 g (31%) of the title compound.

Workup

  1. stirringthe solution was stirred for 2 hours at RT
  2. washThe solution was washed with sat. NaHCO3
  3. customThe milky organic phase was separated
  4. customevaporated to dryness
  5. customThe residue was purified by column chromatography
  6. additionFractions containing the product
  7. customwere evaporated

Sources & evidence

ORD record
ord-0def19f8bb4e46068a97371ccdeb6101
Source dataset
uspto-grants-2012_11
Patent number
US08318779B2

Reaction notes

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