Lithium borohydride → tert-Butyl (2R,4R)-4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate

HRID 2220995Notes

Reaction equation

HRID 2220995 reaction equation
[Li+].[BH4-].[OH:3][C@H:4]1[CH2:8][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C@@H:6]([C:16](OC)=[O:17])[CH2:5]1>C1COCC1>[OH:3][C@H:4]1[CH2:8][N:7]([C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])[C@@H:6]([CH2:16][OH:17])[CH2:5]1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 6951202(2R,4R)-4-Hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Product 1

HCID 10680283tert-Butyl (2R,4R)-4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylateYield 57.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
70 °C

Procedure

LiBH4 (6.46 mmol as a solution in THF) was added to an ice cooled solution of (1,1-dimethylethyl) 2-methyl(2R,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate (0.36 g, 1.47 mmol) in THF. The reaction was heated at 70° C. for 48 hours. The reaction was quenched with isopropanol and then saturated NaHCO3. The mixture was diluted with water and extracted twice with ethyl acetate. The organic layers were washed with 1N NaOH, dried over MgSO4 and concentrated to give 0.185 g of the title compound. 1H NMR 400 MHz, DMSO-D6) δ ppm 1.4 (m, 9 H), 1.8 (m, 1 H), 2.0 (m, 1 H), 3.0 (m, 1 H), 3.4 (m, 1 H), 3.5 (m, 2 H), 3.7 (m, 1 H), 4.1 (m, 1 H), 4.9 (dd, J=5.3, 5.3 Hz, 1 H), 5.1 (m, 1 H).

Workup

  1. customThe reaction was quenched with isopropanol
  2. additionThe mixture was diluted with water
  3. extractionextracted twice with ethyl acetate
  4. washThe organic layers were washed with 1N NaOH
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6b915e16bfbd4f27858f865960b7880f
Source dataset
uspto-grants-2008_05
Patent number
US07368453B2

Reaction notes

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