3-Methylbutanal → HCID 10348294, compound

HRID 2299898Notes

Reaction equation

HRID 2299898 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:32][CH2:33][CH:34]([CH3:36])[CH3:35])[CH:9]2[CH2:14][CH2:13][N:12]([C:15]([C@@H:17]([NH:22][C:23]([N:25]3[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)=[O:24])[CH2:18][CH:19]([CH3:21])[CH3:20])=[O:16])[CH2:11][CH2:10]2)=[CH:4][CH:3]=1.[CH:37](=O)[CH2:38][CH:39]([CH3:41])[CH3:40].[BH-](OC(C)=O)(OC(C)=O)O[C:45](C)=O.[Na+]>C(Cl)Cl.CCOC(C)=O>[CH3:40][C:39]([CH3:41])([CH3:45])[CH2:38][CH2:37][NH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:32][CH2:33][CH:34]([CH3:36])[CH3:35])[CH:9]2[CH2:14][CH2:13][N:12]([C:15]([C@@H:17]([NH:22][C:23]([N:25]3[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)=[O:24])[CH2:18][CH:19]([CH3:21])[CH3:20])=[O:16])[CH2:11][CH2:10]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 115523-MethylbutanalHCID 5049666Sodium triacetoxyborohydrideHCID 44461096HCID 44461096, compound

Product 1

HCID 10348294HCID 10348294, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

(S)-Azepane-1-carboxylic acid (1-{4-[(4-amino-phenyl)-(3-methyl-butyl)-amino]-piperidine-1-carbonyl}-3-methyl-butyl)-amide (Example 35, 0.25 g, 0.50 mmol) was dissolved in CH2Cl2 (4 mL), treated with isovaleraldehyde (63 μL, 0.50 mmol), and stirred for 30 minutes. The reaction was cooled to 0° C., treated with NaBH(OAc)3 (0.16 g, 0.75 mmol), and allowed to warm to room temperature and stir overnight. The reaction was diluted with EtOAc (100 mL), washed with saturated bicarbonate solution and brine, dried over Na2SO4, and concentrated. The residue was chromatographed on silica gel eluting with 4% to 5% MeOH/CH2Cl2 to give the desired product.

Workup

  1. temperatureto warm to room temperature
  2. stirringstir overnight
  3. washwashed with saturated bicarbonate solution and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel eluting with 4% to 5% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-a2d755ebcb074b7da077ff8ee345783b
Source dataset
uspto-grants-2002_12
Patent number
US06495715B2

Reaction notes

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