Boc-Dab(Z)-Ol (S) → tert-butyl[(1S)-3-amino-1-(hydroxymethyl)propyl]carbamate

HRID 269671Notes

Reaction equation

HRID 269671 reaction equation
C(OC(=O)[NH:10][CH2:11][CH2:12][C@H:13]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:14][OH:15])C1C=CC=CC=1>C(O)C.[Pd]>[C:20]([O:19][C:17](=[O:18])[NH:16][C@H:13]([CH2:14][OH:15])[CH2:12][CH2:11][NH2:10])([CH3:23])([CH3:21])[CH3:22]

Participants

4

Reactant 1

HCID 59722512Boc-Dab(Z)-Ol (S)

Product 1

HCID 59722466tert-butyl[(1S)-3-amino-1-(hydroxymethyl)propyl]carbamate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Preparation takes place in analogy to Example 81A from 237 mg (0.7 mmol) of benzyl{(3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxybutyl}carbamate (Example 236A) in 50 ml of ethanol with the addition of 23 mg of palladium on activated carbon (10%).

Workup

  1. customPreparation

Sources & evidence

ORD record
ord-7f6db31506e64e069390104b920f53f4
Source dataset
uspto-grants-2008_11
Patent number
US07446102B2

Reaction notes

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