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

HRID 1941352노트

반응식

HRID 1941352 반응식
[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]

참가 물질

8

반응물 5

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

생성물 2

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-55726ee26f674e34a300e2287dac8cae
출처 데이터셋
uspto-grants-1997_12
특허 번호
US05703129

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