Sodium borohydride → HCID 86695277, compound

HRID 709416Notes

Reaction equation

HRID 709416 reaction equation
[CH:1]([C:3]1[O:7][C:6]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[N:5][N:4]=1)=O.[B-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[CH2:30]([O:37][C:38]1[CH:43]=[CH:42][C:41]([C@@H:44]2[CH2:46][C@H:45]2[NH2:47])=[CH:40][CH:39]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[BH4-].[Na+]>ClC(Cl)C>[CH2:30]([O:37][C:38]1[CH:39]=[CH:40][C:41]([C@@H:44]2[CH2:46][C@H:45]2[NH:47][CH2:1][C:3]2[O:7][C:6]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[N:5][N:4]=2)=[CH:42][CH:43]=1)[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

6

Reactant 4

HCID 4311764Sodium borohydrideHCID 23676153Sodium bis(acetyloxy)boranuidyl acetateHCID 51888238(1R,2S)-2-(4-(Benzyloxy)phenyl)cyclopropan-1-amine2×HCID 86695278HCID 86695278, compound2×

Product 1

HCID 86695277HCID 86695277, compoundYield 15.4%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Tert-butyl (5-formyl-1,3,4-oxadiazol-2-yl)carbamate (Intermediate O, 220 mg, 1.041 mmol) and sodium triacetoxy borohyride (441 mg, 2.08 mmol) was added to a solution of Trans-2-[4-(benzyloxy)phenyl]cyclopropanamine (Intermediate B, 250 mg, 1.041 mmol) in dry Dichloro ethane (2.5 mL) at 0° C. and stirred at RT for 24 h, then the solvent was evaporated. The residue was taken in MeOH (2.5 mL) and NaBH4 (116 mg, 3.138 mmol) was added at 0° C. and stirred for 2 h at RT. After completion, the solvent was evaporated, the residue was taken in water (10 mL) and extracted with EtOAc (4×10 mL) Combined extracts were washed with water (10 mL), brine (10 mL), dried over anhydrous Na2SO4, filtered and evaporated. The residue was purified by column chromatography (SiO2) using MeOH:CHCl3 (1:99) to get tert-butyl (5-((((trans)-2-(4-(benzyloxy)phenyl)cyclopropyl)amino)methyl)-1,3,4-oxadiazol-2-yl)carbamate (70 mg, 15.3%) as pale green liquid.

Workup

  1. customthe solvent was evaporated
  2. stirringstirred for 2 h at RT
  3. customAfter completion, the solvent was evaporated
  4. extractionextracted with EtOAc (4×10 mL)
  5. washwere washed with water (10 mL), brine (10 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by column chromatography (SiO2)

Sources & evidence

ORD record
ord-4f0b6fd902da4b9f9b6e81380aefb843
Source dataset
uspto-grants-2015_11
Patent number
US09181198B2

Reaction notes

Loading…