Lithium borohydride → HCID 86679640, compound

HRID 577695Notes

Reaction equation

HRID 577695 reaction equation
[BH4-].[Li+].C[O:4][C:5]([C@@H:7]1[C@@H:11]([O:12][CH3:13])[CH2:10][N:9]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:8]1)=O>C1COCC1>[C:17]([O:16][C:14]([N:9]1[CH2:10][C@H:11]([O:12][CH3:13])[C@@H:7]([CH2:5][OH:4])[CH2:8]1)=[O:15])([CH3:20])([CH3:19])[CH3:18]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 86679639HCID 86679639, compound

Product 1

HCID 86679640HCID 86679640, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Lithium borohydride (12.7 g, 4 eq) was added portionwise to a solution of (3S,4R)-4-methoxy-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester (35.81 g, 138.1 mmol) in THF (600 mL), then the reaction was heated to 60° C. for 4 hrs. The reaction was quenched with water at 0° C. and extracted with EtOAc. The organic layer was washed with sat. NaCl and dried over Na2SO4. The solvent was removed and the residue was purified through a plug of SiO2 (3:1 EtOAc/heptane) to yield the title compound as a clear oil (29.35 g, 92% yield). 1H NMR (400 MHz, chloroform-d) δ ppm 1.46 (s, 9H) 2.37-2.47 (m, 1H) 3.19 (dd, J=11.08, 5.29 Hz, 1H) 3.33 (d, J=4.03 Hz, 4H) 3.50-3.66 (m, 4H) 3.77-3.83 (m, 1H). m/z (APCI+) for product minus Boc (C6H13NO2) 132.2 (M+H)+. Specific Rotation: [a]D=+9.3 degrees (C=0.86, MeOH).

Workup

  1. customThe reaction was quenched with water at 0° C.
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with sat. NaCl
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed
  6. customthe residue was purified through a plug of SiO2 (3:1 EtOAc/heptane)

Sources & evidence

ORD record
ord-f27d34fe0a034e98b63f721c564b3139
Source dataset
uspto-grants-2015_05
Patent number
US09040547B2

Reaction notes

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