Aluminium lithium hydride → 3-(R)-(1-BOC-2-(S)-pyrrolidinyl)-4-nitrobutanol

HRID 1896Notes

Reaction equation

HRID 1896 reaction equation
[C:1]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C@@H:13]([CH2:20][N+:21]([O-:23])=[O:22])[CH2:14][C:15](OCC)=[O:16])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC>[C:1]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C@@H:13]([CH2:20][N+:21]([O-:23])=[O:22])[CH2:14][CH2:15][OH:16])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 22869541ethyl 3-(R)-(1-BOC-2-(S)-pyrrolidinyl)-4-nitrobutanoate

Product 1

HCID 228695313-(R)-(1-BOC-2-(S)-pyrrolidinyl)-4-nitrobutanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A 7.5 g sample of ethyl 3-(R)-(1-BOC-2-(S)-pyrrolidinyl)-4-nitrobutanoate (prepared according to the procedure of Hayakawa et al., U.S. Pat. No. 5,098,912, issued Mar. 24, 1992) was dissolved in 35 mL of ether and treated with 0.76 g of LAH. After careful quenching of the excess reagents, the title compound was extracted and purified by chromatography (4.5 g).

Workup

  1. customAfter careful quenching of the excess reagents
  2. extractionthe title compound was extracted
  3. custompurified by chromatography (4.5 g)

Sources & evidence

ORD record
ord-bd232c0b8b38439bb9e8a89504c75742
Source dataset
uspto-grants-1998_03
Patent number
US05726182

Reaction notes

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