Lithium borohydride → HCID 86679664, compound

HRID 577721Notes

Reaction equation

HRID 577721 reaction equation
[CH:1]1([C@@H:4]2[CH2:8][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:6][C@H:5]2[C:16](OCC)=[O:17])[CH2:3][CH2:2]1.[Li+].[BH4-]>C1COCC1>[CH:1]1([C@H:4]2[C@H:5]([CH2:16][OH:17])[CH2:6][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:8]2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 86679663HCID 86679663, compound

Product 1

HCID 86679664HCID 86679664, compoundYield 76.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-tert-butyl 3-ethyl(trans)-4-cyclopropylpyrrolidine-1,3-dicarboxylate (9.2 g, 13 mmol) and LiBH4 (1.37 g, 65 mmol) in dry THF (75 mL) was refluxed overnight. TLC (petroleum ether:EtOAc 5:1) indicated the reaction was complete. The reaction mixture was quenched by addition of water (75 mL) and extracted with EtOAc (75 mL). The organic layer was washed with brine (75 mL), dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography (silica gel, petroleum ether:EtOAc=20:1 to 3:1) to give the title compound (2.4 g, 76%) as a yellow oil. 1H NMR (400 MHz, CDCl3): δ ppm 3.80-3.78 (d, 1H), 3.64-3.49 (m, 3H), 3.19-3.07 (m, 2H), 2.21 (s, 1H), 1.94-1.81 (d, 1H), 1.44-1.42 (d, 9H), 1.14-1.23 (m, 1H), 0.67-0.62 (m, 1H), 0.50-0.48 (d, 2H), 0.14-0.08 (m, 2H). m/z (APCI+) for C13H23NO3 186.0 (M−tBu+H)+.

Workup

  1. temperaturewas refluxed overnight
  2. customThe reaction mixture was quenched by addition of water (75 mL)
  3. extractionextracted with EtOAc (75 mL)
  4. washThe organic layer was washed with brine (75 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (silica gel, petroleum ether:EtOAc=20:1 to 3:1)

Sources & evidence

ORD record
ord-be6b1c5e0e8a40d7beb2991ebd94a877
Source dataset
uspto-grants-2015_05
Patent number
US09040547B2

Reaction notes

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