Ethyl Acetate → 4-(S)-cyclohexyl-4-[(5-nitro-2-phenoxy-pyridin-4-ylmethyl)-amino]-butyric acid tert-butyl ester

HRID 491901Notes

Reaction equation

HRID 491901 reaction equation
[C:1]([O:5][C:6](=[O:17])[CH2:7][CH2:8][C@H:9]([NH2:16])[CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)([CH3:4])([CH3:3])[CH3:2].[CH:18]([C:20]1[C:25]([N+:26]([O-:28])=[O:27])=[CH:24][N:23]=[C:22]([O:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:21]=1)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].CCOC(C)=O>C(Cl)Cl>[C:1]([O:5][C:6](=[O:17])[CH2:7][CH2:8][C@@H:9]([CH:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1)[NH:16][CH2:18][C:20]1[C:25]([N+:26]([O-:28])=[O:27])=[CH:24][N:23]=[C:22]([O:29][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:21]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 5049666Sodium triacetoxyborohydride2×HCID 576783284-Formyl-5-nitro-2-phenoxypyridineHCID 670233774-amino-4-(S)-cyclohexyl-butyric acid tert-butyl ester

Product 1

HCID 670236524-(S)-cyclohexyl-4-[(5-nitro-2-phenoxy-pyridin-4-ylmethyl)-amino]-butyric acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-amino-4-(S)-cyclohexyl-butyric acid tert-butyl ester (5 g, 20 mmol) and 4-formyl-5-nitro-2-phenoxypyridine (6 g, 24 mmol) in methylene chloride (100 mL) was stirred at room temperature overnight. NaBH(OAc)3 (0.8 gm, 4 mmol) was added, and the solution was stirred at room temperature for 5 hours. Additional NaBH(OAc)3 (7 g, 33 mmol) was added and the solution was stirred at room temperature for another one hour. The solution was then poured into EtOAc (100 mL). The organic layer washed with aqueous NaCl, dried over MgSO4 and evaporated to yield a residue which was purified by column chromatography (10% EtOAc/Heptane) to yield 4-(S)-cyclohexyl-4-[(5-nitro-2-phenoxy-pyridin-4-ylmethyl)-amino]-butyric acid tert-butyl ester as a brown oil.

Workup

  1. stirringthe solution was stirred at room temperature for another one hour
  2. washThe organic layer washed with aqueous NaCl
  3. dry with materialdried over MgSO4
  4. customevaporated
  5. customto yield a residue which
  6. customwas purified by column chromatography (10% EtOAc/Heptane)

Sources & evidence

ORD record
ord-e7e6b713f8e7406b835d373de3d6d1ca
Source dataset
uspto-grants-2009_05
Patent number
US07531545B2

Reaction notes

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