Isopropanol → HCID 57462501, compound

HRID 2353415Notes

Reaction equation

HRID 2353415 reaction equation
[C:1]([O:5][C:6](=[O:34])[NH:7][C@H:8]1[C@H:13]([C:14]2[CH:19]=[C:18]([F:20])[C:17]([F:21])=[CH:16][C:15]=2[F:22])[CH2:12][CH2:11][C:10]([O:23][Si](C(C)C)(C(C)C)C(C)C)=[CH:9]1)([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(O)(C)C>O1CCCC1.CCCCCCC>[O:23]=[C:10]1[CH2:9][C@H:8]([NH:7][C:6](=[O:34])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3])[C@@H:13]([C:14]2[CH:19]=[C:18]([F:20])[C:17]([F:21])=[CH:16][C:15]=2[F:22])[CH2:12][CH2:11]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-83d8957b2950406c97af15f47a712f7d
Source dataset
uspto-grants-2010_07
Patent number
US07750034B2

Reaction notes

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