tert-butyl N-[(2S)-4-methyl-1-oxopentan-2-yl]carbamate → (s)-[1-(2-Amino-4-methyl-pentyl)-piperidin-4-yl]-(4-benzyloxy-phenyl)-(3-methyl-but-2-enyl)-amine

HRID 1069457Notes

Reaction equation

HRID 1069457 reaction equation
C([NH:8][C@H:9]([CH:14]=O)[CH2:10][CH:11]([CH3:13])[CH3:12])(OC(C)(C)C)=O.[CH2:16]([O:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]([CH2:37][CH:38]=[C:39]([CH3:41])[CH3:40])[CH:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)=[CH:26][CH:25]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl.CCOC(C)=O>[NH2:8][C@@H:9]([CH2:10][CH:11]([CH3:12])[CH3:13])[CH2:14][N:34]1[CH2:33][CH2:32][CH:31]([N:30]([C:27]2[CH:26]=[CH:25][C:24]([O:23][CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[CH:29][CH:28]=2)[CH2:37][CH:38]=[C:39]([CH3:41])[CH3:40])[CH2:36][CH2:35]1

Participants

6

Reactant 3

HCID 104275tert-butyl N-[(2S)-4-methyl-1-oxopentan-2-yl]carbamateHCID 5049666Sodium triacetoxyborohydrideHCID 10641624(4-Benzyloxy-phenyl)-(3-methyl-but-2-enyl)-piperidin-4-yl-amine

Product 1

HCID 11744448(s)-[1-(2-Amino-4-methyl-pentyl)-piperidin-4-yl]-(4-benzyloxy-phenyl)-(3-methyl-but-2-enyl)-amineYield 70.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Boc-L-leucinal (0.78 g, 3.64 mmol) was treated with a solution of (4-Benzyloxy-phenyl)-(3-methyl-but-2-enyl)-piperidin-4-yl-amine (1.28 g, 3.64 mmol) in CH2Cl2 (36 mL), stirred 15 minutes, cooled to 0° C., and treated with NaBH(OAc)3 (1.16 g, 5.46 mmol). The reaction was allowed to warm to RT as ice melted and stir 4 hours. The reaction was diluted with EtOAc (200 mL), washed with saturated bicarbonate solution, and brine, dried over Na2SO4, and concentrated. The residue was chromatographed on silica gel eluting with 8% MeOH/CH2Cl2 to give 1.15 g (57%) of the desired product (Id).

Workup

  1. temperatureto warm to RT as ice
  2. stirringstir 4 hours
  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 8% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-6127116fbb164ad1a4eb469bc0c7d135
Source dataset
uspto-grants-2001_06
Patent number
US06251918B1

Reaction notes

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