HCID 69000025, compound → ((3R,4R,7R)-3-Hydroxy-7-methyl-azepan-4-yl)-carbamic acid tert-butyl ester

HRID 1790656Notes

Reaction equation

HRID 1790656 reaction equation
C(OC([N:11]1[CH2:17][C@@H:16]([OH:18])[C@H:15]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:14][CH2:13][C@H:12]1[CH3:27])=O)C1C=CC=CC=1>CCOC(C)=O.[Pd]>[C:23]([O:22][C:20](=[O:21])[NH:19][C@@H:15]1[CH2:14][CH2:13][C@@H:12]([CH3:27])[NH:11][CH2:17][C@H:16]1[OH:18])([CH3:25])([CH3:24])[CH3:26]

Participants

4

Reactant 1

HCID 69000025HCID 69000025, compound

Product 1

HCID 68998497((3R,4R,7R)-3-Hydroxy-7-methyl-azepan-4-yl)-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

(2R,5R,6R)-5-tert-Butoxycarbonylamino-6-hydroxy-2-methyl-azepane-1-carboxylic acid benzyl ester (0.9 g, 2.4 mmol) was dissolved in EtOAc (40 ml), then 10% Pd/C (0.45 g) was added and the reaction mixture was degasses by bubbling argon for 5 minutes. Then, the reaction was stirred overnight under a balloon filled with hydrogen gas. The reaction mixture was filtered through Celite, concentrated in vacuo by rotary evaporation and was azeotroped with toluene (20 ml), then was used in the next reaction without further purification (0.58 g, quantitative): Electrospray mass spec: M+H+=245.2.

Workup

  1. customby bubbling argon for 5 minutes
  2. additionfilled with hydrogen gas
  3. filtrationThe reaction mixture was filtered through Celite
  4. concentrationconcentrated in vacuo by rotary evaporation
  5. customwas azeotroped with toluene (20 ml)
  6. customwas used in the next reaction without further purification (0.58 g, quantitative)

Sources & evidence

ORD record
ord-e2a9e706079841fc94b1ab2be57b3067
Source dataset
uspto-grants-2006_07
Patent number
US07071184B2

Reaction notes

Loading…