Methanol → [4-Hydroxy-4-(2-methoxy-3-pyridinyl)butyl]carbamic acid 1,1-dimethylethyl ester

HRID 352137Notes

Reaction equation

HRID 352137 reaction equation
B.CB1N2CCC[C@@H]2C(C2C=CC=CC=2)(C2C=CC=CC=2)O1.[CH3:23][C:24]([O:27][C:28](=[O:43])[NH:29][CH2:30][CH2:31][CH2:32][C:33]([C:35]1[C:36]([O:41][CH3:42])=[N:37][CH:38]=[CH:39][CH:40]=1)=[O:34])([CH3:26])[CH3:25].CO>O1CCCC1>[CH3:26][C:24]([O:27][C:28](=[O:43])[NH:29][CH2:30][CH2:31][CH2:32][CH:33]([OH:34])[C:35]1[C:36]([O:41][CH3:42])=[N:37][CH:38]=[CH:39][CH:40]=1)([CH3:23])[CH3:25]

Participants

6

Reactant 4

HCID 887MethanolHCID 6331BoraneHCID 9838490(R)-2-Methyl-CBS-oxazaborolidineHCID 102539314[4-(2-Methoxy-pyridin-3-yl)-4-oxo-butyl]-carbamic acid tert-butyl ester

Product 1

HCID 131724445[4-Hydroxy-4-(2-methoxy-3-pyridinyl)butyl]carbamic acid 1,1-dimethylethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
20 °C

Procedure

Borane (0.7 ml, 1M in tetrahydrofuran) was added to a solution of (3aR)-tetrahydro-1-methyl-3,3-diphenyl-3H-pyrrolo[1,2-c][1,3,2]oxazaborole (0.05 ml, 1M in toluene) in tetrahydrofuran (2 ml) at 0° C. A solution of the product from step (a) above (0.304 g) in tetrahydrofuran (3 ml) was added over 20 minutes and then stirred at 0° C. for 4hand at 20° C. for 14 h. Methanol was added and the solution was evaporated and the residue azeotroped with methanol. Purification by chromatography on silica eluting with petrol-ether gave the sub-title compound as a colourless oil (0.255 g).

Workup

  1. customthe solution was evaporated
  2. customthe residue azeotroped with methanol
  3. customPurification by chromatography on silica eluting with petrol-ether

Sources & evidence

ORD record
ord-62178ffee6644b2eb0ba86da14db1c57
Source dataset
uspto-grants-2004_06
Patent number
US06743939B2

Reaction notes

Loading…