Water → HCID 21460399, compound

HRID 1941221Notes

Reaction equation

HRID 1941221 reaction equation
[N:1]([C:4]1([C:9]([NH:11][CH2:12][CH2:13][O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=O)[CH2:8][CH2:7][CH2:6][CH2:5]1)=[N+]=[N-].[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>O1CCCC1>[CH2:15]([O:14][CH2:13][CH2:12][NH:11][CH2:9][C:4]1([NH2:1])[CH2:8][CH2:7][CH2:6][CH2:5]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 21460408HCID 21460408, compound

Product 1

HCID 21460399HCID 21460399, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of the crude 1-azido-N-(2-benzyloxyethyl)cyclopentan-1-carboxamide 12a (22.3 g) in tetrahydrofuran (100 ml) was added to a suspension of LiAlH4 (6 g) in tetrahydrofuran (100 ml). After reflux for 2 h the mixture was cooled to 0° C. and subsequently treated with water (6 ml), 15% aqueous NaOH (6 ml) and water (6 ml). The mixture was filtered and the precipitate extracted with dichloromethane (200 ml). Drying of the combined organic phases (MgSO4) and evaporation of the solvents in vacuo afforded the title compound as an oil: 18.7 g.

Workup

  1. temperatureAfter reflux for 2 h the mixture
  2. filtrationThe mixture was filtered
  3. extractionthe precipitate extracted with dichloromethane (200 ml)
  4. dry with materialDrying of the combined organic phases (MgSO4) and evaporation of the solvents in vacuo

Sources & evidence

ORD record
ord-9238e56174ae4db2bb59ae47a9ee9e10
Source dataset
uspto-grants-1997_12
Patent number
US05703087

Reaction notes

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