Lithium borohydride → HCID 60067061, compound

HRID 2308097Notes

Reaction equation

HRID 2308097 reaction equation
C[O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([O:10][Si:11]([CH3:14])([CH3:13])[CH3:12])[CH2:7][N:6]1[C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])=O.[Li+].[BH4-]>C1COCC1>[CH2:18]([O:17][C:15]([N:6]1[CH2:7][C@H:8]([O:10][Si:11]([CH3:12])([CH3:13])[CH3:14])[CH2:9][C@H:5]1[CH2:3][OH:2])=[O:16])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 60067078HCID 60067078, compound

Product 1

HCID 60067061HCID 60067061, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To (2S,4R)-4-Trimethylsilanyloxy-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester 1.50 g (4.22 mmol) in 5 mL of anhydrous THF under an atmosphere of Ar in an ice bath, was added 2.56 mL LiBH4 (2.0 M in THF, 5.12 mmol) drop-wise. The solution was stirred for 3 h. The mixture was quenched with 1 mL of Sat. NaHCO3 and EtOAc (50 mL). The organics were washed with Sat. NaHCO3 (2×50 mL). The organic layer was dried over Na2SO4 and the solution was concentrated to afford 1.31 g (96%) of (2S,4R)-2-Hydroxymethyl-4-trimethylsilanyloxy-pyrrolidine-1-carboxylic acid benzyl ester as clear oil. HPLC: Rt 2.87 min. (100% area). 1H NMR (CDCl3, 400 MHz) δ 7.26-7.20 (5H, m), 5.05 (2H, s), 4.47 (1H, d, J=7.4 Hz), 4.20 (1H, bs), 4.08 (1H, q, J=7.3 Hz), 3.64 (1H, t, J=9.1 Hz), 3.51-3.47 (1H, m), 3.41-3.35 (2H, m), 1.89-1.84 (1H, m), 1.57-1.52 (1H, m), 0.11 (9H, s). LCMS (ESI) (M+H+) m/z: 324.2.

Workup

  1. customThe mixture was quenched with 1 mL of Sat. NaHCO3 and EtOAc (50 mL)
  2. washThe organics were washed with Sat. NaHCO3 (2×50 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationthe solution was concentrated

Sources & evidence

ORD record
ord-1477ce41203b4e1c9e64e48f42acd64a
Source dataset
uspto-grants-2004_12
Patent number
US06833456B2

Reaction notes

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