1-Naphthalenemethanamine → HCID 18660163, compound

HRID 1741467Notes

Reaction equation

HRID 1741467 reaction equation
[C:1]1([CH2:11][NH2:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[C:13]([O:17][C:18]([NH:20][C@H:21]([CH:26]=O)[C@H:22]([CH2:24][CH3:25])[CH3:23])=[O:19])([CH3:16])([CH3:15])[CH3:14].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[C:1]1([CH2:11][NH:12][CH2:26][C@@H:21]([NH:20][C:18]([O:17][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:19])[C@@H:22]([CH3:23])[CH2:24][CH3:25])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 83551-NaphthalenemethanamineHCID 5049666Sodium triacetoxyborohydrideHCID 113902721,1-Dimethylethyl N-((1S,2S)-1-formyl-2-methylbutyl)carbamate

Product 1

HCID 18660163HCID 18660163, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a slurry of 1-naphthylmethylamine (5.84 g, 37.2 mmol), crushed 3A molecular sieves (10 g), and N-t-butoxycarbonyl-isoleucinal (8.0 g, 37.2 mmol) in 1,2-dichloroethane (50 ml) was added sodium triacetoxyborohydride (15.8 g, 74.3 mmol) at 0° C. The reaction was allowed to warm slowly to RT and stirred for 48 hrs. The reaction was cooled to 0° C. and quenched with sat. aq. NaHCO3 and stirred for 30 min. The organic layer was separated, washed with saturated brine, dried (MgSO4) and evaporated in vacuo. The residue was purified by flash chromatography (SiO2, 25% ethyl acetate in hexanes) to provide the title compound as an oil.

Workup

  1. temperatureThe reaction was cooled to 0° C.
  2. customquenched with sat. aq. NaHCO3
  3. stirringstirred for 30 min
  4. customThe organic layer was separated
  5. washwashed with saturated brine
  6. dry with materialdried (MgSO4)
  7. customevaporated in vacuo
  8. customThe residue was purified by flash chromatography (SiO2, 25% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-754c1ed319be46359ceebe78b60c127e
Source dataset
uspto-grants-1999_10
Patent number
US05972984

Reaction notes

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