(3S,4S)-1-(2-benzyloxy-3-nitrophenyl)-4-(tert-butyldimethylsilyloxy)-1-penten-3-ol → (3S,4S)-1-(3-amino-2-hydroxyphenyl)-4-(tert-butyldimethylsilyloxy)pentan-3-ol

HRID 2250818Notes

Reaction equation

HRID 2250818 reaction equation
C([O:8][C:9]1[C:14]([N+:15]([O-])=O)=[CH:13][CH:12]=[CH:11][C:10]=1[CH:18]=[CH:19][C@H:20]([OH:31])[C@@H:21]([O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])[CH3:22])C1C=CC=CC=1>CCOC(C)=O.[Pd]>[NH2:15][C:14]1[C:9]([OH:8])=[C:10]([CH2:18][CH2:19][C@H:20]([OH:31])[C@@H:21]([O:23][Si:24]([C:27]([CH3:29])([CH3:28])[CH3:30])([CH3:26])[CH3:25])[CH3:22])[CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 1

HCID 69102620(3S,4S)-1-(2-benzyloxy-3-nitrophenyl)-4-(tert-butyldimethylsilyloxy)-1-penten-3-ol

Product 1

HCID 69103771(3S,4S)-1-(3-amino-2-hydroxyphenyl)-4-(tert-butyldimethylsilyloxy)pentan-3-olYield 99.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (3S,4S)-1-(2-benzyloxy-3-nitrophenyl)-4-(tert-butyldimethylsilyloxy)-1-penten-3-ol (P0015; 610 mg) and 10% Pd—C (120 mg) in EtOAc (6 ml) was stirred under hydrogen atmosphere at atmospheric pressure for 1 hour. Pd—C was removed by filtration through Celite. The filtrate was filtered through silica gel (6 g) and evaporated to give (3S,4S)-1-(3-amino-2-hydroxyphenyl)-4-(tert-butyldimethylsilyloxy)pentan-3-ol (P0016; 444.9 mg) as a brown solid.

Workup

  1. customPd—C was removed by filtration through Celite
  2. filtrationThe filtrate was filtered through silica gel (6 g)
  3. customevaporated

Sources & evidence

ORD record
ord-68b84fe9b9724a73a3ffeca230045acd
Source dataset
uspto-grants-2008_01
Patent number
US07317107B2

Reaction notes

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