Cyclopentanol → cis-Phenylmethyl 5-{[(cyclopentyloxy)carbonyl]amino}-2-methyl-1-piperidinecarboxylate

HRID 2367438Notes

Reaction equation

HRID 2367438 reaction equation
[CH3:1][C@H:2]1[N:7]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:6][C@@H:5](C(O)=O)[CH2:4][CH2:3]1.[CH:21]1([OH:26])[CH2:25][CH2:24][CH2:23][CH2:22]1.C([N:29]([CH2:32]C)CC)C.P(N=[N+]=[N-])(OC1C=CC=CC=1)(OC1C=CC=CC=1)=[O:35]>CCOC(C)=O>[CH:21]1([O:26][C:32]([NH:29][C@H:5]2[CH2:6][N:7]([C:8]([O:10][CH2:11][C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)=[O:9])[C@@H:2]([CH3:1])[CH2:3][CH2:4]2)=[O:35])[CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

6

Reactant 4

HCID 7298CyclopentanolHCID 8471TriethylamineHCID 123414Diphenylphosphoryl azideHCID 51357693(3S,6R)-1-((benzyloxy)carbonyl)-6-methylpiperidine-3-carboxylic acid

Product 1

HCID 131731328cis-Phenylmethyl 5-{[(cyclopentyloxy)carbonyl]amino}-2-methyl-1-piperidinecarboxylateYield 61.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of cis-6-methyl-1-{[(phenylmethyl)oxy]carbonyl}-3-piperidinecarboxylic acid (200 mg, 0.721 mmol), cyclopentyl alcohol (1.5 mL, 16.51 mmol), and triethylamine (0.151 mL, 1.082 mmol) was added slowly diphenyl azidophosphate (dppa) (0.171 mL, 0.793 mmol), and the reaction mixture was stirred at room temperature for 15 minutes, and then at 125° C. After 4 hr, the reaction was diluted with EtOAc (40 mL) and washed with water. The organic was then dried over MgSO4, filtered, concentrated and purified with Biotage SNAP 10 g column with gradient of 0 to 50% EtOAc in hexane over 35 minutes to afford the title compound (160 mg) as a clear oil. LC-MS (ES) m/z=361 [M+H]+.

Workup

  1. customat 125° C
  2. waitAfter 4 hr
  3. washwashed with water
  4. dry with materialThe organic was then dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified with Biotage SNAP 10 g column with gradient of 0 to 50% EtOAc in hexane over 35 minutes

Sources & evidence

ORD record
ord-b63bb086a7394cd9b8f0197e222f47d7
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

Loading…