Aluminium lithium hydride → 5-Oxo-4-(3-oxo-propyl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester

HRID 1096241Notes

Reaction equation

HRID 1096241 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12](=[O:15])[N:11]([CH2:16][CH2:17][C:18](=[O:23])N(OC)C)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12](=[O:15])[N:11]([CH2:16][CH2:17][CH:18]=[O:23])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86638389HCID 86638389, compound

Product 1

HCID 866158685-Oxo-4-(3-oxo-propyl)-[1,4]diazepane-1-carboxylic acid tert-butyl esterYield 61.7%

Procedure

To a cooled (−78° C.) solution of 4-[2-(methoxy-methyl-carbamoyl)-ethyl]-5-oxo-[1,4]diazepane-1-carboxylic acid tert-butyl ester 3 g (9 mmol) was added dropwise a solution of lithium aluminum hydride 9.1 ml (9 mmol, 1 M solution in THF). The mixture was quenched by addition of acetone and then AcOH. The reaction was allowed to reach RT after which time water and 10% aq. KHSO4 solution were added and the mixture repeatedly extracted with TBME. The combined organic was washed with brine, dried (MgSO4) and concentrated. Purification by flash column chromatography (EtOAc:MeOH 19:1) afforded the title compound 1.5 g (61%) as a colorless oil. MS: 271.5 (MH+).

Workup

  1. customThe mixture was quenched by addition of acetone
  2. customto reach RT
  3. additionwere added
  4. extractionthe mixture repeatedly extracted with TBME
  5. washThe combined organic was washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customPurification by flash column chromatography (EtOAc:MeOH 19:1)

Sources & evidence

ORD record
ord-06f0cf07475a460e95392e046906da2d
Source dataset
uspto-grants-2012_03
Patent number
US08138175B2

Reaction notes

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