Formic Acid → HCID 67058341, compound

HRID 471433Notes

Reaction equation

HRID 471433 reaction equation
C(N(CC)CC)C.C(O)=O.[F:11][C:12]([F:25])([F:24])[O:13][C:14]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:15]=1[CH2:16][CH2:17][C:18]2=[O:23].O>ClCCl>[F:11][C:12]([F:24])([F:25])[O:13][C:14]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:15]=1[CH2:16][CH2:17][C@@H:18]2[OH:23]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 962WaterHCID 8471TriethylamineHCID 61382921HCID 61382921, compound

Product 1

HCID 67058341HCID 67058341, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Triethylamine (5.23 mL, 37.2 mmol) is dissolved in dichloromethane (60 mL) and cooled to 0° C. then formic acid (1.60 mL, 42.4 mmol) is added dropwise with cooling. 4-Trifluoromethoxy-indan-1-one (US patent 2011/53974, 2.58 g, 11.94 mmol) is added and the mixture degassed with a flow of argon. Chloro([(1S,2S)-(+2-amino-1,2-diphenylethyl]-4-toluenesulfonyl)amido)(mesitylene)ruthenium(II) complex (148 mg, 0.24 mmol) is added and the mixture is stirred overnight under argon at room temperature. Water is added, the mixture shaken and the phases separated. The organic phase is dried and concentrated under vacuum. The residue is purified by flash chromatography (20% ethyl acetate in cyclohexane) to give the title compound (yield 2.50 g).

Workup

  1. temperaturewith cooling
  2. customthe mixture degassed with a flow of argon
  3. additionChloro([(1S,2S)-(+2-amino-1,2-diphenylethyl]-4-toluenesulfonyl)amido)(mesitylene)ruthenium(II) complex (148 mg, 0.24 mmol) is added
  4. stirringthe mixture shaken
  5. customthe phases separated
  6. customThe organic phase is dried
  7. concentrationconcentrated under vacuum
  8. customThe residue is purified by flash chromatography (20% ethyl acetate in cyclohexane)

Sources & evidence

ORD record
ord-0b728c8919804df7a141895ab91fbe30
Source dataset
uspto-grants-2014_01
Patent number
US08633182B2

Reaction notes

Loading…