Sodium borohydride → HCID 178521040, compound

HRID 2361666Notes

Reaction equation

HRID 2361666 reaction equation
[CH:1]1([N:5]2[CH2:11][CH2:10][CH2:9][N:8]([C:12]([CH:14]3[CH2:17][C:16](=[O:18])[CH2:15]3)=[O:13])[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.[BH4-].[Na+]>CO>[CH:1]1([N:5]2[CH2:11][CH2:10][CH2:9][N:8]([C:12]([C@@H:14]3[CH2:17][C@H:16]([OH:18])[CH2:15]3)=[O:13])[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 44477247HCID 44477247, compound

Product 1

HCID 178521040HCID 178521040, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 3-[(4-cyclobutyl-1,4-diazepan-1-yl)carbonyl]cyclobutanone (50 mg, 0.2 mmol) in MeOH (2.5 ml) at 0° C. was added NaBH4 (3.7 mg, 0.1 mmol). After 10 mins the reaction mixture was warmed to RT and stirred for a further 1 h. The solvent was evaporated in vacuuo and the crude solid was partitioned between DCM and 0.5 M NaOH. The organic phase was separated, dried (Na2SO4), filtered and concentrated at reduced pressure. The resulting yellow oil was purified by silica gel FCC (eluant DCM.MeOH/NH3 90:10:1) to provide the title compound as off white solid (35 mg, 70%).

Workup

  1. customThe solvent was evaporated in vacuuo
  2. customthe crude solid was partitioned between DCM and 0.5 M NaOH
  3. customThe organic phase was separated
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated at reduced pressure
  7. customThe resulting yellow oil was purified by silica gel FCC (eluant DCM.MeOH/NH3 90:10:1)

Sources & evidence

ORD record
ord-fe8ad654933449ccb8e8ee555327e6ae
Source dataset
uspto-grants-2014_04
Patent number
US08691804B2

Reaction notes

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