Lithium borohydride → HCID 86756662, compound

HRID 1976238Notes

Reaction equation

HRID 1976238 reaction equation
C[O:2][C:3](=O)[C@@H:4]1[CH2:8][C@@H:7]([O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11])[CH2:6][N:5]1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[N+:23]([O-:25])=[O:24].[BH4-].[Li+]>O1CCCC1>[Si:10]([O:9][C@H:7]1[CH2:6][N:5]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[N+:23]([O-:25])=[O:24])[C@H:4]([CH2:3][OH:2])[CH2:8]1)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 57150476HCID 57150476, compound

Product 1

HCID 86756662HCID 86756662, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2S, 4R)-4-(tert-butyldimethylsilyloxy)-1-(2-nitrophenyl) proline methyl ester (9.62 g) obtained in Reference Example 40 ml anhydrous tetrahydrofuran (300 ml), there was added, in small portions, 0.96 g of lithium borohydride under ice-cooling. After stirring the reaction liquid at room temperature over 15 hours, it was poured into ice water and then extracted with ethyl acetate. The organic phase thus obtained was washed with water, dried over anhydrous magnesium sulfate and then concentrated. The residue thus obtained was subjected to silica gel column chromatography and then eluted with ethyl acetate/hexane (1/9) to give 8.55 g (yield 96.1%) of the title compound.

Workup

  1. temperaturecooling
  2. customthe reaction liquid at room temperature over 15 hours
  3. extractionextracted with ethyl acetate
  4. customThe organic phase thus obtained
  5. washwas washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue thus obtained
  9. washeluted with ethyl acetate/hexane (1/9)

Sources & evidence

ORD record
ord-d69405f105334d0d918a1e3862a624f9
Source dataset
uspto-grants-2001_05
Patent number
US06225306B1

Reaction notes

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