(1s)-Camphanoyl chloride → HCID 131732062, compound

HRID 339221Notes

Reaction equation

HRID 339221 reaction equation
[I:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([CH:10]([OH:15])[C:11]([CH3:14])([CH3:13])[CH3:12])=[C:4]([N+:16]([O-:18])=[O:17])[CH:3]=1.[C@:19]12([CH3:31])[C:25]([CH3:27])([CH3:26])[CH:22]([CH2:23][CH2:24]1)[CH2:21][CH:20]2[C:28](Cl)=[O:29]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C@:19]12([CH3:31])[C:25]([CH3:26])([CH3:27])[CH:22]([CH2:23][CH2:24]1)[CH2:21][CH:20]2[C:28]([O:15][CH:10]([C:5]1[CH:6]=[C:7]([O:8][CH3:9])[C:2]([I:1])=[CH:3][C:4]=1[N+:16]([O-:18])=[O:17])[C:11]([CH3:14])([CH3:13])[CH3:12])=[O:29]

Participants

5

Reactant 2

HCID 71432218(1s)-Camphanoyl chlorideHCID 89566844HCID 89566844, compound

Product 1

HCID 131732062HCID 131732062, compoundYield 84.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of racemic (R/S)-1-(4-iodo-5-methoxy-2-nitrophenyl)-2,2-dimethyl-1-propanol (395 mg, 1.1 mmol) and DMAP (263 mg, 2.16 mmol) in anhydrous CH2Cl2 (5.0 mL), (1S)-camphanic chloride (Corrie et al., 1992, which is incorporated by reference) (350 mg, 1.62 mmol) was added, and the mixture was stirred overnight at room temperature under a nitrogen atmosphere. The reaction mixture was diluted with CH2Cl2 (50 mL) and washed with saturated NaHCO3 solution (50 mL). The organic phase was dried over Na2SO4, concentrated in vacuo, and the residue was purified by silica gel column chromatography to yield (R/S)-1-(4-iodo-5-methoxy-2-nitrophenyl)-2,2-dimethyl-1-propyl (1S)-camphanate (490 mg, 80%, 1:1 mixture of diastereomers).

Workup

  1. washwashed with saturated NaHCO3 solution (50 mL)
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-eb71be9ee7014b3da484629f21a20bdb
Source dataset
uspto-grants-2014_11
Patent number
US08889860B2

Reaction notes

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