Water → HCID 67148943, compound

HRID 2428151Notes

Reaction equation

HRID 2428151 reaction equation
[BH4-].[Na+].[C:3]([O:7][C:8](=[O:23])[N:9]([CH2:13][C:14]1[CH:19]=[C:18]([CH:20]=[O:21])[CH:17]=[CH:16][C:15]=1[Cl:22])[CH:10]1[CH2:12][CH2:11]1)([CH3:6])([CH3:5])[CH3:4].O>CC#N>[C:3]([O:7][C:8](=[O:23])[N:9]([CH2:13][C:14]1[CH:19]=[C:18]([CH2:20][OH:21])[CH:17]=[CH:16][C:15]=1[Cl:22])[CH:10]1[CH2:11][CH2:12]1)([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 86632369HCID 86632369, compound

Product 1

HCID 67148943HCID 67148943, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

NaBH4 (1.48 g, 37.7 mmol) was added to a sol. of (2-chloro-5-formyl-benzyl)-cyclopropyl-carbamic acid tert-butyl ester (11.7 g, 37.7 mmol) in CH3CN (113 mL) under N2. The mixture was stirred at rt for 1 h, and water (113 mL) was added. The mixture was stirred at rt for 5 min, and extracted with CH2Cl2 (3×). The combined org. layers were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the crude by FC (heptane/EtOAc 7:3) yielded the title compound (6.53 g, 56%). LC-MS: tR=0.96 min; ES+: 297.37.

Workup

  1. stirringThe mixture was stirred at rt for 5 min
  2. extractionextracted with CH2Cl2 (3×)
  3. dry with materiallayers were dried over MgSO4
  4. filtrationfiltered
  5. customthe solvents were removed under reduced pressure
  6. customPurification of the crude by FC (heptane/EtOAc 7:3)

Sources & evidence

ORD record
ord-d6b0e39e37eb4ee2ba95698ca236c11d
Source dataset
uspto-grants-2011_06
Patent number
US07968720B2

Reaction notes

Loading…