Borane;tetrahydrofuran → HCID 131729309, compound

HRID 657132Notes

Reaction equation

HRID 657132 reaction equation
[CH3:1][C:2]([Si:5]([CH3:27])([CH3:26])[O:6][C@H:7]1[CH2:12][N:11]([C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[CH2:10][C@@H:9]([C:23](O)=[O:24])[CH2:8]1)([CH3:4])[CH3:3].B.C1COCC1>C1COCC1>[CH3:4][C:2]([Si:5]([CH3:27])([CH3:26])[O:6][C@H:7]1[CH2:8][C@@H:9]([CH2:23][OH:24])[CH2:10][N:11]([C:13]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[O:14])[CH2:12]1)([CH3:1])[CH3:3]

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 68810552HCID 68810552, compound

Product 1

HCID 131729309HCID 131729309, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To cis-(3RS,5RS)-5-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-1-{[(phenylmethyl)oxy]carbonyl}-3-piperidinecarboxylic acid (0.80 g; 2.0 mmol) in THF (20 ml) was added 1N BH3.THF in THF (6.0 ml; 6.0 mmol) and the reaction was allowed to stir at room temperature under N2 for 6 h. Excess borane was quenched by the addition of MeOH and the reaction was allowed to stir for 2 hours. The reaction was partitioned between EtOAc (150 ml) and water (25 ml) the layers were separated and the organic layer was washed with brine and dried with Na2SO4. The solvents were removed and the crude residue was purified by chromatography on silica gel using a 0-10% MeOH/DCM gradient to provide the desired compound (550 mg; 73%) as a colorless oil.

Workup

  1. customExcess borane was quenched by the addition of MeOH
  2. stirringto stir for 2 hours
  3. customThe reaction was partitioned between EtOAc (150 ml) and water (25 ml) the layers
  4. customwere separated
  5. washthe organic layer was washed with brine
  6. dry with materialdried with Na2SO4
  7. customThe solvents were removed
  8. customthe crude residue was purified by chromatography on silica gel using a 0-10% MeOH/DCM gradient

Sources & evidence

ORD record
ord-6770e37147df4c7c86ac675364ea5480
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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