Isopropanol → HCID 66976603, compound

HRID 1022826Notes

Reaction equation

HRID 1022826 reaction equation
[C:1]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(O)C.[Cl:24][C:25]1[CH:26]=[C:27]([C@H:32]2[C@@H:38]([CH:39]=O)[O:37][CH2:36][CH2:35][N:34]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:33]2)[CH:28]=[CH:29][C:30]=1[Cl:31].C[Si](C=[N+]=[N-])(C)C>O1CCCC1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Rh]>[Cl:24][C:25]1[CH:26]=[C:27]([C@H:32]2[C@@H:38]([CH:39]=[CH2:1])[O:37][CH2:36][CH2:35][N:34]([C:41]([O:43][C:44]([CH3:46])([CH3:47])[CH3:45])=[O:42])[CH2:33]2)[CH:28]=[CH:29][C:30]=1[Cl:31]

Participants

7

Reactant 4

HCID 3776IsopropanolHCID 11776TriphenylphosphineHCID 167693TrimethylsilyldiazomethaneHCID 86663883HCID 86663883, compound

Product 1

HCID 66976603HCID 66976603, compoundYield 55.3%

Reagents, catalysts & solvents 2

HCID 84599Chlorotris(triphenylphosphine)rhodium(I)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of chlorotris(triphenylphosphine)rhodium (I) (0.12 g) and triphenylphosphine (1.5 g) in tetrahydrofuran (5 ml) was added 2-propanol (0.44 ml), and tert-butyl (6R,7S)-6-(3,4-dichlorophenyl)-7-formyl-1,4-oxazepane-4-carboxylate (2.0 g) was added. To the reaction mixture was added trimethylsilyldiazomethane (2 M diethyl ether solution, 5.2 ml), and the mixture was stirred at room temperature overnight. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound (1.1 g).

Workup

  1. additionwas added
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ff3c743d327b4a4eb741d6a12a25023f
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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