Lithium borohydride → HCID 66970916, compound

HRID 1361313Notes

Reaction equation

HRID 1361313 reaction equation
[C:1]([N:8]1[CH2:12][C@@H:11]([N:13]([CH:20]2[CH2:25][CH2:24][C:23]([CH3:27])([CH3:26])[CH2:22][CH2:21]2)[C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:10][C@@:9]1(C)[C:28]([O-])=[O:29])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[Li+].[BH4-]>C1COCC1>[C:1]([N:8]1[CH2:12][C@@H:11]([N:13]([CH:20]2[CH2:25][CH2:24][C:23]([CH3:27])([CH3:26])[CH2:22][CH2:21]2)[C:14](=[O:19])[C:15]([CH3:17])([CH3:18])[CH3:16])[CH2:10][C@H:9]1[CH2:28][OH:29])([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 86636640HCID 86636640, compound

Product 1

HCID 66970916HCID 66970916, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 1-BOC-2-methyl-(2S,4S)-4-[(4,4-dimethylcyclohexyl)(2,2-dimethylpropanoyl)amino]pyrrolidine-2-carboxylate (1.18 g, 2.71 mmol) prepared in Step B of Example A1 in THF (10 ml) was added LiBH4 (177 mg, 8.13 mmol). The solution was stirred at 70° C. for 2 h, concentrated in vacuo, and extracted with EtOAc. The organic extracts were washed with a saturated NaHCO3 aqueous solution and brine, dried over MgSO4, and concentrated in vacuo to give the title compound (0.88 g, 81%).

Workup

  1. concentrationconcentrated in vacuo
  2. extractionextracted with EtOAc
  3. washThe organic extracts were washed with a saturated NaHCO3 aqueous solution and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-96439d835bed447c92ad0203189e1b85
Source dataset
uspto-grants-2011_02
Patent number
US07879852B2

Reaction notes

Loading…