Lithium tri-s-butylborohydride → 4-Benzyl-5-(2-tert-butylcarbamoyl-5-hydroxy-cyclohexylmethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

HRID 987922Notes

Reaction equation

HRID 987922 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:12]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:11]([CH2:20][CH:21]2[CH2:26][C:25](=[O:27])[CH2:24][CH2:23][CH:22]2[C:28](=[O:34])[NH:29][C:30]([CH3:33])([CH3:32])[CH3:31])[O:10][C:9]1([CH3:36])[CH3:35])=[O:7])([CH3:4])([CH3:3])[CH3:2].CCC(C)[BH-](C(C)CC)C(C)CC.[Li+]>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH:12]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:11]([CH2:20][CH:21]2[CH2:26][CH:25]([OH:27])[CH2:24][CH2:23][CH:22]2[C:28](=[O:34])[NH:29][C:30]([CH3:33])([CH3:32])[CH3:31])[O:10][C:9]1([CH3:36])[CH3:35])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 3611392Lithium tri-s-butylborohydrideHCID 698539384-Benzyl-5-(2-tert-butylcarbamoyl-5-oxo-cyclohexylmethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Product 1

HCID 698535414-Benzyl-5-(2-tert-butylcarbamoyl-5-hydroxy-cyclohexylmethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl esterYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

A solution of 4-benzyl-5-(2-tert-butylcarbamoyl-5-oxo-cyclohexylmethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (980 mg, 1.96 mmol) in dry tetrahydrofuran was stirred at −78° C. under nitrogen during the addition of 1 M L-selectride solution in tetrahydrofuran (2.5 ml, 2.5 mmol). The resulting mixture was stirred at −78° C. for 30 minutes and then quenched by the addition of saturated aqueous ammonium chloride solution and allowed to warm to room temperature. The layers were separated and the aqueous phase was extracted with ethyl acetate. The combined organic phases were washed with 2N aqueous hydrogen chloride solution and brine, dried (anhydrous magnesium sulfate) and concentrated in vacuo. Purification by flash chromatography on silica gel (ethyl acetate/hexane: 7/3 to 1/0) provided of 4-benzyl-5-(2-tert-butylcarbamoyl-5-hydroxy-cyclohexylmethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (934 mg, 95%) as a white foam.

Workup

  1. customquenched by the addition of saturated aqueous ammonium chloride solution
  2. temperatureto warm to room temperature
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted with ethyl acetate
  5. washThe combined organic phases were washed with 2N aqueous hydrogen chloride solution and brine
  6. dry with materialdried (anhydrous magnesium sulfate)
  7. concentrationconcentrated in vacuo
  8. customPurification by flash chromatography on silica gel (ethyl acetate/hexane: 7/3 to 1/0)

Sources & evidence

ORD record
ord-990bf18e6bc14c01824e26fa9ae151ad
Source dataset
uspto-grants-2003_10
Patent number
US06632826B1

Reaction notes

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