HCID 89524690, compound → HCID 89533825, compound

HRID 920235Notes

Reaction equation

HRID 920235 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:18][C:17]2[C:16]([C:19](O)=[O:20])=[CH:15][CH:14]=[CH:13][C:12]=2[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C1COCC1>[OH:20][CH2:19][C:16]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:17]=1[CH2:18][CH:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[CH2:10][CH2:11]2

Participants

3

Reactant 1

HCID 89524690HCID 89524690, compound

Product 1

HCID 89533825HCID 89533825, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a flask was added 7-((tert-butoxycarbonyl)amino)-5,6,7,8-tetrahydro-naphthalene-1-carboxylic acid (20-1) (2.02 g, 6.93 mmol), then anhydrous THF (20 mL). The reaction mixture was cooled to 0 C (ice water bath) while stirring under an atmosphere of nitrogen. Then a 1M solution of BORANE TETRAHYDROFURAN COMPLEX (30 mL, 30.0 mmol) was added dropwise while stirring. The reaction mixture was stirred at 0 C for 1.5 hours. Followed by LC/MS. The reaction mixture was then uncapped (always at 0 C), then quenched by dropwise addition of saturated NH4Cl (lots of bubbling/gas evolution). The reaction mixture was then warmed to room temperature, then suspended in EtOAc, separated, the organics were then washed with saturated NaHCO3, then H2O, then brine; dried over Na2SO4, filtered & concentrated. The resulting residue was purified by silica gel chromatography (0-50% EtOAc/Hex; 80 g ISCO); desired fractions concentrated to yield tert-butyl (8-(hydroxymethyl)-1,2,3,4-tetrahydronaphthalen-2-yl)carbamate (20-2).

Workup

  1. stirringwhile stirring
  2. stirringThe reaction mixture was stirred at 0 C for 1.5 hours
  3. customuncapped (always at 0 C), then quenched by dropwise addition of saturated NH4Cl (lots of bubbling/gas evolution)
  4. customseparated
  5. washthe organics were then washed with saturated NaHCO3
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe resulting residue was purified by silica gel chromatography (0-50% EtOAc/Hex; 80 g ISCO)
  10. concentrationdesired fractions concentrated

Sources & evidence

ORD record
ord-2dd20b4cda474005be052f584920b88d
Source dataset
uspto-grants-2016_03
Patent number
US09273040B2

Reaction notes

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