Lithium borohydride → HCID 117702498, compound

HRID 1503254Notes

Reaction equation

HRID 1503254 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]12[CH2:16][C:13]([C:17](OC)=[O:18])([CH2:14][CH2:15]1)[CH2:12][CH2:11][CH2:10]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[BH4-]>C1COCC1>[OH:18][CH2:17][C:13]12[CH2:16][C:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])([CH2:15][CH2:14]1)[CH2:10][CH2:11][CH2:12]2

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 84082986HCID 84082986, compound

Product 1

HCID 117702498HCID 117702498, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 5-(tert-butoxycarbonylamino)bicyclo[3.2.1]octane-1-carboxylate (7.8 g, 27.6 mmol) in THF (65 mL) was added LiBH4 (2.0 M in THF, 28 mL, 56.0 mmol) dropwise at 0° C. under N2. The solution was warmed up to room temperature gradually and stirred overnight. The reaction mixture was quenched with Sat. NH4Cl and extracted with ethyl acetate (3×150 mL). The combined organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure to afford 7.0 g (90%) of the crude title compound, tert-Butyl 5-(hydroxymethyl)bicyclo[3.2.1]octan-1-ylcarbamate, as colorless oil, which was used in the next step without further purification. ESI-MS m/z: 200 (M-55)+.

Workup

  1. customThe reaction mixture was quenched with Sat. NH4Cl
  2. extractionextracted with ethyl acetate (3×150 mL)
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d07bbbce258b46b6aa516c42c9173f04
Source dataset
uspto-grants-2015_12
Patent number
US09212165B2

Reaction notes

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