3-Methylbutanal → HCID 57277639, compound

HRID 2299894Notes

Reaction equation

HRID 2299894 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][CH:16]2[CH2:21][CH2:20][N:19]([C:22]([C@@H:24]([NH:29][C:30]([N:32]3[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]3)=[O:31])[CH2:25][CH:26]([CH3:28])[CH3:27])=[O:23])[CH2:18][CH2:17]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:39](=O)[CH2:40][CH:41]([CH3:43])[CH3:42].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl.CCOC(C)=O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]([CH2:42][CH:41]([CH3:43])[CH2:40][CH3:39])[CH:16]2[CH2:21][CH2:20][N:19]([C:22]([C@@H:24]([NH:29][C:30]([N:32]3[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]3)=[O:31])[CH2:25][CH:26]([CH3:28])[CH3:27])=[O:23])[CH2:18][CH2:17]2)=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 115523-MethylbutanalHCID 5049666Sodium triacetoxyborohydrideHCID 10697309HCID 10697309, compound

Product 1

HCID 57277639HCID 57277639, compoundYield 169.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

(S)-Azepane-1-carboxylic acid {1-[4-(4-benzyloxy-phenylamino)-piperidine-1-carbonyl]-3-methyl-butyl}-amide (Example 28) (0.30 g, 0.28 mmol) was dissolved in CH2Cl2 (5 mL) and treated with isovaleraldehyde (62 μL, 0.58 mmol). The reaction was stirred for 30 minutes at RT, then cooled to 0° C., treated with NaBH(OAc)3, allowed to warm to room temperature as the ice melted and stir overnight. The reaction was then 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 3:2 hexane/EtOAc to give 0.28 g (82%) of the desired product.

Workup

  1. temperaturecooled to 0° C.
  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 3:2 hexane/EtOAc

Sources & evidence

ORD record
ord-a5997f63164f4032b16f660af4c46369
Source dataset
uspto-grants-2002_12
Patent number
US06495715B2

Reaction notes

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