N-Iodosuccinimide → HCID 90041487, compound

HRID 929181Notes

Reaction equation

HRID 929181 reaction equation
[C:1]([O:4][C@@H:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C@H:6]1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=[O:3])[CH3:2].[I:17]N1C(=O)CCC1=O>C(O)(C(F)(F)F)=O>[C:1]([O:4][C@@H:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C@H:6]1[C:11]1[CH:16]=[CH:15][C:14]([I:17])=[CH:13][CH:12]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 11009435trans-Racemic-2-phenylcyclohexyl acetate

Product 1

HCID 90041487HCID 90041487, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a stirred solution of trans-racemic-2-phenylcyclohexyl acetate (5.60 g, 25.7 mmol) under nitrogen in TFA (50 ml) at 0° C. was added N-iodosuccinimide (5.77 g, 25.7 mmol) portionwise over 5 minutes. The mixture was allowed to warm and stir at room temperature for 3 hours. The mixture was concentrated under reduced pressure. The resultant oil was chromatographed using an 80 g silica gel cartridge eluted with 0-20% ethyl acetate in hexanes over 15 column volumes. The desired product fractions were combined and concentrated under reduced pressure to provide the desired product as a yellow oil. LC-MS: calculated for C14H17IO2 344.19 observed m/e: 345.33 (M+H)+ (Rt 2.60/4 min).

Workup

  1. temperatureto warm
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customThe resultant oil was chromatographed
  4. washeluted with 0-20% ethyl acetate in hexanes over 15 column volumes
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d17b8046538c4ca4af1701e6dbd5ac80
Source dataset
uspto-grants-2016_03
Patent number
US09290517B2

Reaction notes

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