Tetrafluoroboric acid → HCID 117894078, compound

HRID 592111Notes

Reaction equation

HRID 592111 reaction equation
[F:1][CH:2]([F:24])[O:3][C:4]1[CH:23]=[CH:22][C:7]([C:8]([NH:10][C:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C:12]=2[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[O:9])=[CH:6][CH:5]=1.F[B-](F)(F)F.[H+].[H][H]>CO>[F:1][CH:2]([F:24])[O:3][C:4]1[CH:5]=[CH:6][C:7]([C:8]([NH:10][C@@H:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C@@H:12]2[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[O:9])=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 28118Tetrafluoroboric acidHCID 117841203HCID 117841203, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 117894078HCID 117894078, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a 120 ml pressure resistant vessel were charged ethyl 2-{4-(difluoromethoxy)benzoyl}aminocyclohexene-1-carboxylate <5.0 g, 14.7 mmol>, diacetato{(S)-2,2′-bis[bis(3,5-di-tert-butyl-4-methoxyphenyl)phosphino]-1,1′-binaphthyl}ruthenium (II) (0.125 g, 0.0886 mmol), 42% tetrafluoroboric acid (14.3 ml, 0.1772 mmol) and methanol (25 ml) and the mixture was stirred. Thereafter, hydrogen (1 MPa) was filled therein, and the mixture was stirred at 45° C. for 40 hr. After confirmation of the completion of hydrogen absorption, the ordinary pressure was restored, and the mixture was concentrated into a diastereomer/enantiomer mixture to give the title compound as white crystals. yield 5.0 g. NMR data of (1S,2R) form 1H NMR (CDCl3) δ1.27 (3H, t, J=7.1 Hz), 1.4-1.9 (7H, m), 2.1-2.3 (1H, m), 2.8-2.9 (1H, m), 4.1-4.4 (3H, m), 6.56 (1H, t, J=76.6 Hz), 7.15 (2H, d, J=8.7 Hz)

Workup

  1. stirringthe mixture was stirred at 45° C. for 40 hr
  2. customAfter confirmation of the completion of hydrogen absorption
  3. concentrationthe mixture was concentrated into a diastereomer/enantiomer mixture

Sources & evidence

ORD record
ord-72939820cd014608be00e69ecf8f6f85
Source dataset
uspto-grants-2016_01
Patent number
US09238667B2

Reaction notes

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