Methyl 1-amino-1-cyclopentanecarboxylate (H-Ac5c-OMe) → Methyl 1-({3-[(tert-butoxycarbonyl)amino]-2-phenylpropyl}amino)cyclopentanecarboxylate

HRID 1890721Notes

Reaction equation

HRID 1890721 reaction equation
O=[CH:2][CH:3]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9].[NH2:19][C:20]1([C:25]([O:27][CH3:28])=[O:26])[CH2:24][CH2:23][CH2:22][CH2:21]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)(Cl)Cl.C(Cl)Cl.C(=O)(O)[O-].[Na+]>[C:8]([O:7][C:6]([NH:5][CH2:4][CH:3]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:2][NH:19][C:20]1([C:25]([O:27][CH3:28])=[O:26])[CH2:24][CH2:23][CH2:22][CH2:21]1)=[O:12])([CH3:11])([CH3:10])[CH3:9]

Participants

7

Reactant 3

HCID 231225Methyl 1-amino-1-cyclopentanecarboxylate (H-Ac5c-OMe)HCID 5049666Sodium triacetoxyborohydrideHCID 11414003tert-Butyl (3-oxo-2-phenylpropyl)carbamate

Product 1

HCID 58550617Methyl 1-({3-[(tert-butoxycarbonyl)amino]-2-phenylpropyl}amino)cyclopentanecarboxylate

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Into a solution of tert-butyl (3-oxo-2-phenylpropyl)carbamate from Step B (0.5 g, 2 mmol) in dry chloroform (20 mL) was added methyl 1-amino-1-cyclopentanecarboxylate (0.431 g, 3.01 mmol). After 15 minutes, sodium triacetoxyborohydride (0.893 g, 4.21 mmol) was added. After 4 hours of stirring at ambient temperature, the reaction mixture was diluted with DCM and 5% sodium bicarbonate. The layers were separated and the aqueous layer was extracted once with DCM. The combined organics were dried over sodium sulfate, filtered, and concentrated in vacuo to yield a residue, which was subjected to a normal phase chromatography, eluting with a gradient of 1-6% methanol in DCM. Concentration of the fractions containing the product provided the title compound. MS: m/z=377 (M+1).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted once with DCM
  3. dry with materialThe combined organics were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto yield a residue, which
  7. washeluting with a gradient of 1-6% methanol in DCM
  8. additionConcentration of the fractions containing the product

Sources & evidence

ORD record
ord-f2c4eb9b3f67496db16af66486442f38
Source dataset
uspto-grants-2013_08
Patent number
US08507477B2

Reaction notes

Loading…