Benzyl [(1S)-4-[(tert-butoxycarbonyl)amino]-1-(2-hydroxyethyl)butyl]carbamate → tert-Butyl [(4S)-4-amino-6-hydroxyhexyl]carbamate

HRID 1441983Notes

Reaction equation

HRID 1441983 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][C@H:12]([NH:16]C(=O)OCC1C=CC=CC=1)[CH2:13][CH2:14][OH:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[NH2:16][C@H:12]([CH2:13][CH2:14][OH:15])[CH2:11][CH2:10][CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 53795716Benzyl [(1S)-4-[(tert-butoxycarbonyl)amino]-1-(2-hydroxyethyl)butyl]carbamate

Product 1

HCID 57440195tert-Butyl [(4S)-4-amino-6-hydroxyhexyl]carbamate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

620 mg (1.69 mmol) of benzyl [(1S)-4-[(tert-butoxycarbonyl) -amino]-1-(2-hydroxyethyl)butyl]-carbamate (Example Z2) are dissolved in 60 ml of ethanol. 100 mg of palladium on activated carbon (10%) are added thereto, and the mixture is hydrogenated under atmospheric pressure at RT for 15 h. The reaction mixture is filtered through prewashed kieselguhr, washed with ethanol, and the filtrate is concentrated on a rotary evaporator. The product is reacted without further purification.

Workup

  1. filtrationThe reaction mixture is filtered through prewashed kieselguhr
  2. washwashed with ethanol
  3. concentrationthe filtrate is concentrated on a rotary evaporator
  4. customThe product is reacted without further purification

Sources & evidence

ORD record
ord-4c18f1d927504850879554268c0c1f8f
Source dataset
uspto-grants-2010_02
Patent number
US07655643B2

Reaction notes

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