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

HRID 1941352ノート

反応式

HRID 1941352 の反応式
[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]

参加物

8

反応物 5

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

生成物 2

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

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-55726ee26f674e34a300e2287dac8cae
出典データセット
uspto-grants-1997_12
特許番号
US05703129

反応ノート

読み込み中…