Lithium borohydride → HCID 57947516, compound

HRID 416402Notes

Reaction equation

HRID 416402 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:16][O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[CH2:10][CH2:11][C:12](OC)=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[BH4-]>C1COCC1.CO>[Si:18]([O:17][CH2:16][C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:10][CH2:11][CH2:12][OH:13])([C:21]([CH3:23])([CH3:24])[CH3:22])([CH3:20])[CH3:19]

Participants

5

Reactant 2

HCID 4148881Lithium borohydrideHCID 13355203HCID 13355203, compound

Product 1

HCID 57947516HCID 57947516, compoundYield 106.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-methyl 4-(tert-butoxycarbonylamino)-5-(tert-butyldimethylsilyloxy)pentanoate (40 g, 0.111 mol) in THF (100 mL) and MeOH (5.0 mL) was added LiBH4 (2M in THF, 56.0 mL, 0.112 mol) at 0° C. The reaction mixture was stirred at RT for 2 h. The reaction mixture was cooled to 0° C. and slowly quenched with saturated NaHCO3 solution. The resulting mixture was stirred RT overnight and filtered. The solid was washed with EtOAc. The combined filtrate was diluted with an additional EtOAc (200 mL). The organic layer was washed with water and brine, dried over Na2SO4, filtered, and concentrated to give (S)-tert-butyl 1-(tert-butyldimethylsilyloxy)-5-hydroxypentan-2-ylcarbamate (39.5 g), which was used without further purification. LRMS (M+Na+) m/z 356.4.2.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. customslowly quenched with saturated NaHCO3 solution
  3. stirringThe resulting mixture was stirred RT overnight
  4. filtrationfiltered
  5. washThe solid was washed with EtOAc
  6. additionThe combined filtrate was diluted with an additional EtOAc (200 mL)
  7. washThe organic layer was washed with water and brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-574ae1c7551a4e84b64e8e1e6ff120d9
Source dataset
uspto-grants-2012_01
Patent number
US08088793B2

Reaction notes

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