Potassium Hydroxide → HCID 131728772, compound

HRID 2075024Notes

Reaction equation

HRID 2075024 reaction equation
[C:1]([SiH2:5][O:6][C:7]([CH3:27])([CH3:26])[C:8]1[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[CH:10][C:9]=1[C:18]([CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)=[O:19])([CH3:4])([CH3:3])[CH3:2].[OH-].[K+]>C(O)(C)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2CN[C@@H]2CCCC[C@H]2NCC2C=CC=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:1]([SiH2:5][O:6][C:7]([CH3:27])([CH3:26])[C:8]1[CH:13]=[C:12]([C:14]([F:16])([F:17])[F:15])[CH:11]=[CH:10][C:9]=1[C@H:18]([CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)[OH:19])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 131728773HCID 131728773, compound

Product 1

HCID 131728772HCID 131728772, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 10909155(1R,2R)-N1,N2-Bis(2-(diphenylphosphino)benzyl)cyclohexane-1,2-diamineCatalystHCID 3776IsopropanolSolvent2×

Procedure

A mixture of [IrHCl2(COD)]2 (33 mg, 0.044 mmol) and (1R,2R)—N,N′-bis[2-(diphenylphosphino)benzyl]cyclohexane-1,2-diamine (29 mg, 0.044 mmol) in isopropanol (37 ml) was stirred at room temperature for 30 minutes. A solution of [2-(tert-butyl-dimethyl-silanyloxymethyl)-4-trifluoromethyl-phenyl]-cyclohexyl-methanone (1.6 g, 4 mmol) in isopropanol (5 ml) was added to mixture followed by potassium hydroxide (28 mg, 0.5 mmol) and stirred for 16 hours. Isopropanol was removed in vacuo and the residue was purified by chromatography over 25+M Biotage silica column eluted with ethyl acetate in heptanes 0% (1 CV), 2-20% (10CV), 20% (2CV) to yield the title compound (1.4 g, 87%) as colorless oil. 1H NMR (400 MHz, CDCl3) δ ppm 0.09 (s, 6H) 0.9 (s, 9H) 1.2 (m, 3H) 1.6 (d, J=7.4 Hz, 1H) 1.7 (m, 4H) 2.0 (m, 1H) 2.2 (m, 1H) 2.4 (m, 1H) 4.5 (m, 1H) 4.7 (d, J=13.7 Hz, 1H) 4.8 (d, J=13.7 Hz, 1H) 7.5 (d, J=1.2 Hz, 2H) 7.6 (s, 1H). Chiral SFC, Retention timet=1.93 min. indicates product is 95.0% ee. [α]D20=−12.99 deg (c=9.5 mg/mL, acetone)

Workup

  1. stirringstirred for 16 hours
  2. customIsopropanol was removed in vacuo
  3. customthe residue was purified by chromatography over 25+M Biotage silica column
  4. washeluted with ethyl acetate in heptanes 0% (1 CV), 2-20% (10CV), 20% (2CV)

Sources & evidence

ORD record
ord-bcd5807e85034e568c0eeefa7d7103cd
Source dataset
uspto-grants-2011_04
Patent number
US07919506B2

Reaction notes

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