Lithium borohydride → HCID 86596907, compound

HRID 1374368Notes

Reaction equation

HRID 1374368 reaction equation
[O:1]=[C:2]1[C@@H:8]2[CH2:9][C@@H: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 17039450HCID 17039450, compound

Product 1

HCID 86596907HCID 86596907, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A sample of benzyl (1R,2S,5R)-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-5d68e850b1194834aaa8f8605c14d479
Source dataset
uspto-grants-2007_01
Patent number
US07163937B2

Reaction notes

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