Isopropanol → HCID 57462501, compound

HRID 1454786Notes

Reaction equation

HRID 1454786 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[C@H:10]1[C@H:15]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH:14]=[C:13]([O:24][Si](C(C)C)(C(C)C)C(C)C)[CH2:12][CH2:11]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(O)(C)C>O1CCCC1.CCCCCCC>[O:24]=[C:13]1[CH2:14][C@H:15]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:20])[CH3:21])[C@@H:10]([C:3]2[CH:4]=[C:5]([F:9])[C:6]([F:8])=[CH:7][C:2]=2[F:1])[CH2:11][CH2:12]1

Participants

6

Reactant 3

HCID 3776IsopropanolHCID 2724141Tetrabutylammonium FluorideHCID 131727249HCID 131727249, compound

Product 1

HCID 57462501HCID 57462501, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8900HeptaneSolvent

Procedure

To a round-bottomed flask (500 mL) containing trans tert-butyl (6-(2,4,5-trifluorophenyl)-3-[(triisopropylsilyl)oxy]cyclohex-2-en-1-yl)carbamate (10.7 g) dissolved in tetrahydrofuran (100 mL), tetrabutylammonium fluoride (1M in tetrahydrofuran, 26 mL) was added and the mixture was stirred for 1 h. The solution was concentrated to a dark brown oil and purified by chromatography (silica gel, gradient 20%-40% ethyl acetate in hexane) to yield the product as a mixture of enantiomers. HPLC using a chiral AD column (12% isopropanol in heptane) gave the title compound as the slower eluting isomer. LC/MS 227.1 (M+1).

Workup

  1. concentrationThe solution was concentrated to a dark brown oil
  2. custompurified by chromatography (silica gel, gradient 20%-40% ethyl acetate in hexane)
  3. customto yield the product
  4. additionas a mixture of enantiomers

Sources & evidence

ORD record
ord-23f36c3758d84f139542d035fba02f7b
Source dataset
uspto-grants-2009_01
Patent number
US07482336B2

Reaction notes

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