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

HRID 229840Notes

Reaction equation

HRID 229840 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-067fa554f62746e4a8fa227ed6819af4
Source dataset
uspto-grants-2009_07
Patent number
US07563784B2

Reaction notes

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