Water → HCID 58557262, compound

HRID 1969866Notes

Reaction equation

HRID 1969866 reaction equation
[CH2:1]([N:8]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:9]12[CH2:16][CH2:15][C:12]([C:17](OC)=[O:18])([CH2:13][CH2:14]1)[CH2:11][CH2:10]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Li+].O>C1COCC1.CCOC(C)=O>[CH2:1]([N:8]([C:9]12[CH2:14][CH2:13][C:12]([CH2:17][OH:18])([CH2:11][CH2:10]1)[CH2:15][CH2:16]2)[C:21](=[O:22])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 4148881Lithium borohydrideHCID 58557870HCID 58557870, compound

Product 1

HCID 58557262HCID 58557262, compoundYield 92.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 4-(benzyl(tert-butoxycarbonyl)amino)bicyclo[2.2.2]octane-1-carboxylate (2.70 g, 7.23 mmol) in THF (24 mL) at about 0° C. was added lithium borohydride (0.350 g, 14.46 mmol). The reaction mixture was warmed to ambient temperature and stirred for about 16 h. The reaction was cooled to about 0° C. and water (15 mL) was carefully added. The reaction mixture was warmed to ambient temperature and was diluted with EtOAc (20 mL). The layers were separated and the organic layer was washed with brine (2×20 mL), dried over anhydrous Na2SO4, filtered and concd under reduced pressure to provide tert-butyl benzyl(4-(hydroxymethyl)bicyclo[2.2.2]octan-1-yl)carbamate (2.31 g, 92%) as an off white sticky foam: LC/MS (Table 1, Method b) Rt=2.67 min; MS m/z: 346 (M+H)+.

Workup

  1. temperatureThe reaction was cooled to about 0° C.
  2. temperatureThe reaction mixture was warmed to ambient temperature
  3. customThe layers were separated
  4. washthe organic layer was washed with brine (2×20 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered

Sources & evidence

ORD record
ord-fd8f16533c16424894bdff771fccf2ba
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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