Trifluoroacetate → HCID 58622182, compound

HRID 2220707Notes

Reaction equation

HRID 2220707 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:16]2[C@@H:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)[CH2:10][C@H:9]1[CH:17]=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(O[BH-](O[C:29](=[O:31])[CH3:30])OC(=O)C)(=O)C.[Na+].F[C:34](F)(F)[C:35]([O-])=O>ClCCl>[C:1]([O:5][C:6]([N:8]1[C@@H:16]2[C@@H:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)[CH2:10][C@H:9]1[CH2:17][NH:8][CH2:9][C:10]1[O:31][C:29]2[CH:30]=[CH:35][CH:34]=[CH:13][C:12]=2[CH:11]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 84468TrifluoroacetateHCID 5049666Sodium triacetoxyborohydrideHCID 58622148HCID 58622148, compound

Product 1

HCID 58622182HCID 58622182, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 31 mg (0.12 mmol) of (2S,3aS,7aS)-2-formyl-octahydro-indole-1-carboxylic acid tert-butyl ester in 1 mL dichloromethane, 18 mg (0.12 mmol) of c-benzofuran-2-yl-methylamine 40 mg (0.18 mmol) of sodium triacetoxyborohydride were added and the mixture was stirred for 3 hours, then diluted with 5 mL dichloromethane and quenched with 3 mL of aqueous sodium bicarbonate. The aqueous layer was extracted once with dichloromethane and the combined organic layers were dried with anhydrous magnesium sulfate, evaporated in vacuum and purified using reverse phase HPLC, mobile phase with a gradient 15-80% acetonitrile in 50 min. Fractions containing pure product were evaporated in vacuum to yield, 53 mg of white solid as the trifluoroacetate. LC-MSD, m/z for C23H32N2O3 [M+H]+: 385.2.

Workup

  1. customquenched with 3 mL of aqueous sodium bicarbonate
  2. extractionThe aqueous layer was extracted once with dichloromethane
  3. dry with materialthe combined organic layers were dried with anhydrous magnesium sulfate
  4. customevaporated in vacuum
  5. custompurified
  6. customin 50 min
  7. additionFractions containing pure product
  8. customwere evaporated in vacuum
  9. customto yield

Sources & evidence

ORD record
ord-2361666ecd15416ebfb2f293f4962cf8
Source dataset
uspto-grants-2008_08
Patent number
US07417062B2

Reaction notes

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