Isocaproaldehyde → N-Butyl-gamma-hydroxy-alpha-methyl-delta-[(4-methylpentyl)amino]cyclohexanehexanamide hydrochloride

HRID 1941352Notes

Reaction equation

HRID 1941352 reaction equation
[NH2:1][CH:2]([CH2:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)[CH:3]([OH:14])[CH2:4][CH:5]([CH3:13])[C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH3:12])=[O:7].[CH3:22][CH:23]([CH3:28])[CH2:24][CH2:25][CH:26]=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+].C(Cl)[Cl:49]>C(O)(=O)C>[NH4+:1].[OH-:7].[ClH:49].[CH2:9]([NH:8][C:6](=[O:7])[CH:5]([CH3:13])[CH2:4][CH:3]([OH:14])[CH:2]([NH:1][CH2:26][CH2:25][CH2:24][CH:23]([CH3:28])[CH3:22])[CH2:15][CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1)[CH2:10][CH2:11][CH3:12]

Participants

8

Reactant 5

HCID 129IsocaproaldehydeHCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 19908509delta-Amino-N-butyl-gamma-hydroxy-alpha-methyl-cyclohexanehexanamide

Product 2

HCID 14923Ammonium HydroxideHCID 67684627N-Butyl-gamma-hydroxy-alpha-methyl-delta-[(4-methylpentyl)amino]cyclohexanehexanamide hydrochlorideYield 59%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of [αS-(αR*,γR*,δR*)]δ-amino-N-butyl-γ-hydroxy-α-methyl-cyclohexanehexanamide (II: 0.17 g, 0.57 mmol) and 4-methylvaleraldehyde (0.063 g, 0.63 mmol) in CH2Cl2 (3 mL) was added NaBH(OAc)3 (0.181 g, 0.86 mmol) and glacial acetic acid (0.05 mL). The mixture was stirred at r.t. for 16 h. The reaction was made basic (pH=8) by the addition of sat aqueous NaHCO3 and extracted with CH2Cl2. The organic extracts were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. Silica gel chromatography (19:19:1 0.05 CHCl3 :Et2O:MeOH:NH4OH) of the concentrate gave the free amine (0.128 g, 59%) which was converted to its hydrochloride salt by the addition of 1.5N ethanolic HCl (0.3 mL). Removal of solvent in vacuo gave the title compound (0.128 g, 59%) as an amorphous white solid, mp 65° C.

Workup

  1. extractionextracted with CH2Cl2
  2. washThe organic extracts were washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-55726ee26f674e34a300e2287dac8cae
Source dataset
uspto-grants-1997_12
Patent number
US05703129

Reaction notes

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