Sodium triacetoxyborohydride → HCID 58005166, compound

HRID 1879257Notes

Reaction equation

HRID 1879257 reaction equation
[Cl-].[CH3:2][O:3][C:4](=[O:11])[C@@H:5]([NH3+:10])[C:6]([CH3:9])([CH3:8])[CH3:7].C(O[BH-](O[C:22](=O)[CH3:23])OC(=O)C)(=O)C.[Na+]>ClCCCl.C(Cl)Cl>[CH2:4]([NH:10][C@H:5]([C:4]([O:3][CH3:2])=[O:11])[C:6]([CH3:9])([CH3:8])[CH3:7])[CH2:5][CH2:6][CH2:7][CH:22]=[CH2:23]

Participants

5

Reactant 2

HCID 5049666Sodium triacetoxyborohydrideHCID 178501514HCID 178501514, compound

Product 1

HCID 58005166HCID 58005166, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

Hex-5-enal 98 (obtained from hex-5-en-1-ol via a PCC oxidation) (0.95 eq.) was added at RT to a 0.11 M solution of (2S)-1-methoxy-3,3-dimethyl-1-oxobutan-2-aminium chloride (1.0 eq.) and TEA (1.0 eq.) in DCE. Sodium triacetoxyborohydride (1.0 eq.) was added in one portion and the reaction mixture was stirred at RT overnight. The reaction mixture was diluted with DCM/saturated aqueous NaHCO3. The phases were separated; the organic layer was washed with brine, dried (Na2SO4) and filtered though a short path of silica gel (PE:EtOAc=9:1) to afford the title compound 99 as a pale yellow liquid (72%). 1H NMR (300 MHz, CDCl3, 300 K) δ 5.89-5.71 (m, 1H), 5.07-4.88 (m, 2H), 3.71 (s, 3H), 2.88 (s, 1H), 2.62-2.48 (m, 1H), 2.45-2.31 (m, 1H), 2.13-1.98 (m, 2H), 1.67-1.54 (m, 1H), 1.53-1.35 (m, 4H), 0.95 (s, 9H).

Workup

  1. customThe phases were separated
  2. washthe organic layer was washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered though a short path of silica gel (PE:EtOAc=9:1)

Sources & evidence

ORD record
ord-735edd6f721648388dad71ba5f365026
Source dataset
uspto-grants-2012_11
Patent number
US08314062B2

Reaction notes

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