(3aS)-1-methyl-3,3-diphenyl-hexahydropyrrolo(1,2-c)(1,3,2)oxazaborole → Methyl 4-{2-[(2R)-2((1E,3R,7R)-7-{[tert-butyl(dimethyl)silyl]oxy}-3-hydroxyoct-1-enyl)-5-oxopyrrolidin-1-yl}ethyl}benzoate

HRID 28781Notes

Reaction equation

HRID 28781 reaction equation
B1(C)OC(C2C=CC=CC=2)(C2C=CC=CC=2)[C@H]2N1CCC2.[Si:22]([O:29][C@H:30]([CH3:56])[CH2:31][CH2:32][CH2:33][C:34](=[O:55])/[CH:35]=[CH:36]/[C@H:37]1[CH2:41][CH2:40][C:39](=[O:42])[N:38]1[CH2:43][CH2:44][C:45]1[CH:54]=[CH:53][C:48]([C:49]([O:51][CH3:52])=[O:50])=[CH:47][CH:46]=1)([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23]>C1COCC1>[Si:22]([O:29][C@H:30]([CH3:56])[CH2:31][CH2:32][CH2:33][C@@H:34]([OH:55])/[CH:35]=[CH:36]/[C@H:37]1[CH2:41][CH2:40][C:39](=[O:42])[N:38]1[CH2:43][CH2:44][C:45]1[CH:54]=[CH:53][C:48]([C:49]([O:51][CH3:52])=[O:50])=[CH:47][CH:46]=1)([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23]

Participants

4

Reactant 2

HCID 2734713(3aS)-1-methyl-3,3-diphenyl-hexahydropyrrolo(1,2-c)(1,3,2)oxazaboroleHCID 69250684Methyl 4-{2-[(2R)-2((1E,7R)-7-{[tert-butyl(dimethyl)silyl]oxy}-3-oxooct-1-enyl)-5-oxopyrrolidin-1-yl}ethyl}benzoate

Product 1

HCID 69250171Methyl 4-{2-[(2R)-2((1E,3R,7R)-7-{[tert-butyl(dimethyl)silyl]oxy}-3-hydroxyoct-1-enyl)-5-oxopyrrolidin-1-yl}ethyl}benzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (S)-2-methyl-CBS-oxazaborolidine (1.0 M in toluene, 0.4 mL, 0.4 mmol) in anhydrous THF (10 mL) at 0° C. was added Borane-THF complex (1.0 M, 0.4 mL, 0.4 mmol) dropwise. The mixture was stirred for 15 minutes. Methyl 4-{2-[(2R)-2((1E,7R)-7-{[tert-butyl(dimethyl)silyl]oxy}-3-oxooct-1-enyl)-5-oxopyrrolidin-1-yl}ethyl}benzoate (200 mg, 0.4 mmol) in THF (1 mL) was added dropwise. The mixture was stirred for 3 hours. The mixture was quenched with addition of 1 mL of the saturated ammonia chloride and was dilute with EtOAc (20 mL). The organic layer was washed with brine (3×5 mL), dried over MgSO4. The residue was used for the next reaction without purification.

Workup

  1. stirringThe mixture was stirred for 3 hours
  2. customThe mixture was quenched with addition of 1 mL of the saturated ammonia chloride
  3. additionwas dilute with EtOAc (20 mL)
  4. washThe organic layer was washed with brine (3×5 mL)
  5. dry with materialdried over MgSO4
  6. customThe residue was used for the next reaction without purification

Sources & evidence

ORD record
ord-e499d458169c4d3d946c9f5fea107cb4
Source dataset
uspto-grants-2008_09
Patent number
US07419999B2

Reaction notes

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