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

HRID 1450100Notes

Reaction equation

HRID 1450100 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-f9b731babdff4b92a19d4947559595b7
Source dataset
uspto-grants-1997_02
Patent number
US05599816

Reaction notes

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