(R)-4-(3-Benzyloxy-propyl)-2-methyl-5-oxo-[1,4]diazepane-1-carboxylic acid tert-butyl ester → (R)-4-(3-Hydroxy-propyl)-2-methyl-5-oxo-[1,4]diazepane-1-carboxylic acid tert-butyl ester

HRID 655562Notes

Reaction equation

HRID 655562 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12](=[O:15])[N:11]([CH2:16][CH2:17][CH2:18][O:19]CC2C=CC=CC=2)[CH2:10][C@H:9]1[CH3:27])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12](=[O:15])[N:11]([CH2:16][CH2:17][CH2:18][OH:19])[CH2:10][C@H:9]1[CH3:27])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 67080753(R)-4-(3-Benzyloxy-propyl)-2-methyl-5-oxo-[1,4]diazepane-1-carboxylic acid tert-butyl ester

Product 1

HCID 67080704(R)-4-(3-Hydroxy-propyl)-2-methyl-5-oxo-[1,4]diazepane-1-carboxylic acid tert-butyl esterYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 0.650 g (1.73 mmol) of (R)-4-(3-benzyloxy-propyl)-2-methyl-5-oxo-[1,4]diazepane-1-carboxylic acid tert-butyl ester (example 1A) in 30 ml methanol was treated with 0.065 g of Pd/C (10%) and was stirred over H2-atmosphere over night. After filtration, the solution was evaporated, reevaporated (3 times) with toluene and the solvent was removed under vacuum to give 0.485 g (98%) of the title compound as colorless oil. MS: 287.1 (MH+).

Workup

  1. filtrationAfter filtration
  2. customthe solution was evaporated
  3. customreevaporated (3 times) with toluene
  4. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-7c30b1c39e4046eba3fee410591bd661
Source dataset
uspto-grants-2011_12
Patent number
US08071586B2

Reaction notes

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