Sodium borohydride → Tert-butyl 4-(1-aminopropyl)-2-nitrobenzoate

HRID 554824Notes

Reaction equation

HRID 554824 reaction equation
[N+:1]([C:4]1[CH:16]=[C:15]([C:17](=O)[CH2:18][CH3:19])[CH:14]=[CH:13][C:5]=1[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])([O-:3])=[O:2].[BH4-].[Na+].O.[NH3:24]>N.C(O)C.C(O[Ti](OC(C)C)(OC(C)C)OC(C)C)(C)C>[NH2:24][CH:17]([C:15]1[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[C:4]([N+:1]([O-:3])=[O:2])[CH:16]=1)[CH2:18][CH3:19]

Participants

6

Reactant 3

HCID 4311764Sodium borohydrideHCID 12896473Azane;hydrateHCID 66935244Tert-butyl 2-nitro-4-propionylbenzoate

Product 1

HCID 67461906Tert-butyl 4-(1-aminopropyl)-2-nitrobenzoate

Reagents, catalysts & solvents 2

HCID 178460666HCID 178460666, compoundCatalystHCID 22020343Ethanol, reaction products with ammonia, distn. residuesSolvent

Procedure

Tert-butyl 2-nitro-4-propionylbenzoate (9.2 g) was suspended in 2N ammonia/ethanol solution (81 ml), then tetraisopropoxytitanium (18.7 ml) was added at room temperature and the mixture was stirred at that temperature for 6 hours. Next, sodium borohydride (1.8 g) was added to the mixture, and the resulting mixture was stirred at that temperature for 16 hours. Then 2.1N ammonia water (81 ml) and Celite (9g) were added to the reaction solution and the inspluble materials were filtered off and washed with water and ethyl acetate. The filtrate was concentrated in vacuo, then a 5N aqueous sodium hydroxide solution and ethyl acetate were added to the obtained residue. The separated organic layer was concentrated in vacuo, then the obtained residue was purified by silica gel column chromatography to obtain the title compound (7.6 g) as an oily substance.

Workup

  1. stirringthe resulting mixture was stirred at that temperature for 16 hours
  2. filtrationthe inspluble materials were filtered off
  3. washwashed with water and ethyl acetate
  4. concentrationThe filtrate was concentrated in vacuo
  5. additiona 5N aqueous sodium hydroxide solution and ethyl acetate were added to the obtained residue
  6. concentrationThe separated organic layer was concentrated in vacuo
  7. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9fdd327512614da6b1a8fe56fa00f978
Source dataset
uspto-grants-2011_11
Patent number
US08049006B2

Reaction notes

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