Lithium borohydride → HCID 86596907, compound

HRID 1455463Notes

Reaction equation

HRID 1455463 reaction equation
[O:1]=[C:2]1[C@@H:8]2[CH2:9][CH:4]([CH2:5][CH2:6][C@@H:7]2[NH:10][C:11](=[O:20])[O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[O:3]1.[Li+].[BH4-]>C1COCC1>[OH:3][C@@H:4]1[CH2:5][CH2:6][C@H:7]([NH:10][C:11](=[O:20])[O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C@H:8]([CH2:2][OH:1])[CH2:9]1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 86610536HCID 86610536, compound

Product 1

HCID 86596907HCID 86596907, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A sample of benzyl (1R,2S,SR)-7-oxo-6-oxa-bicyclo[3.2.1]octan-2-ylcarbamate (2.8 g) was dissolved in anhydrous THF prior to the addition of LiBH4 (0.44 g) in one portion. The reaction mixture was stirred at rt overnight. The reaction was quenched with saturated NH4Cl and extracted with EtOAc. The organic layer was washed with brine and dried (MgSO4). Filtered, concentrated and chromatographed to get benzyl (1S,2R,4R)-4-hydroxy-2-(hydroxymethyl)cyclohexylcarbamate as a white foamy solid.

Workup

  1. customThe reaction was quenched with saturated NH4Cl
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationFiltered
  6. concentrationconcentrated
  7. customchromatographed

Sources & evidence

ORD record
ord-2d4e59bcd36f4b5d86d233bdde33f475
Source dataset
uspto-grants-2009_01
Patent number
US07482335B2

Reaction notes

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